Bifunctionalized allenes. Part XXI. Electrophilic cyclization and addition reactions of 3-(α- or β-hydroxyalkyl)-allenylphosphonates and allenyl phosphine oxides

References

• (a) Bates, R. W.; Satcharoen, V. Nucleophilic Transition Metal based Cyclization of Allenes. Chem. Soc. Rev. 2002, 31, 12–21. (b) Ma, S. Recent Advances in the Chemistry of Allenes. Aldrichim. Acta. 2007, 40, 91–102. (c) Hassan, H. H. A. M. Recent Progress in the Chemistry of Allenes. Curr. Org. Synth. 2007, 4, 413–439. (d) Pinho e Melo, T. M. V. D. Allenes as Dipolarophiles and 1,3-Dipole Precursors: Synthesis of Carbocyclic and Heterocyclic Compounds. Curr. Org. Chem. 2009, 13, 1406–1431. (e) Back, T. G.; Clary, K. N.; Gao, D. Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones. Chem. Rev. 2010, 110, 4498–4553.
   PubMed Web of Science ®Google Scholar
• (a) De la Mare, P. B. D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam, The Netherlands, 1966; pp. 250–266. (b) Caserio, M. C. Selectivity in Addition Reactions of Allenes. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; John Wiley & Sons: New York, NY, 1970; pp. 239–299. (c) De la Mare, P. B. D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam, The Netherlands, 1982; pp. 317–325. (d) Jacobs, T. L. Electrophilic Addition to Allenes. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, NY, USA, 1982; Vol. 2, pp. 417–510. (e) Smadja, W. Electrophilic Addition to Allenic Derivatives: Selectivity, Regio- and Stereochemistry and Mechanisms. Chem. Rev. 1983, 83, 263–320. (f) Ma, S. Ionic Addition to Allenes. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp. 595–699.
   Google Scholar
• (a) Angelov, C. M. Reactivity of Sulfuryl Chloride in Reaction with 1,2-Alkadienephosphonates. Zh. Obshch. Khim. 1980, 50, 2448–2452. (b) Angelov, C. M.; Stoianov, N. M.; Ionin, B. I. Halogenation of 5-Methyl-1,3,4-Hexatriene-3-Phosphonic Dialkyl Esters. Zh. Obshch. Khim. 1982, 52, 178–181. (c) Angelov, Ch. M.; Christov, Ch. Z. Synthesis of 3-Vinyl-2,5-Dihidro-1,2-Oxaphophole-2-Oxides. Synthesis 1984, 664–667. (d) Yu, F.; Lian, X.; Zhao, J.; Yu, Y.; Ma, S. CuX2-Mediated Halolactonization Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids and their Suzuki Cross-Coupling Reaction. J. Org. Chem. 2009, 74, 1130–1134. (e) Angelov, C. M. Five-membered Heterocyclization of Phosphorus-containing Allenes by their Reaction with Electrophiles-Possibilities and Restrictions. Phosphorus Sulfur. 1983, 15, 177–193. (f) Khusainova, N. G.; Pudovik, A. N. Phosphorylated Allenes. Methods of Synthesis and Properties. Russ. Chem. Rev. 1987, 56, 564–578. (g) Alabugin, I. V.; Brel, V. K. Phosphorylated Allenes: Structure and Interaction with Electrophilic Reagents. Russ. Chem. Rev. 1997, 66, 205–224.
   Google Scholar
• (a) Kalek, M.; Johansson, T.; Jezowska, M.; Stawinski, J. Palladium-Catalyzed Propargylic Substitution with Phosphorus Nucleophiles: Efficient, Stereoselective Synthesis of Allenylphosphonates and Related Compounds. Org. Lett. 2010, 12, 4702–4702. (b) Wua, C.; Yeb, F.; Wub, G.; Xub, S.; Deng, G.; Zhang, Y.; Wang, J. Synthesis of Allenylphosphonates through Cu(l)-Catalyzed Coupling of Terminal Alkynes with Diazophosphonates. Synthesis. 2016, 48, 751–760. (c) Gangadhararao, G.; Prasad Tulichala, R. N.; Kumara Swamy, K. C. Spontaneous Resolution upon Crystallization of Allenyl-bis-Phosphine Oxides. Chem. Commun. 2015, 51, 7168–7171. (d) Sajna, K. V.; Kotikalapudi, R.; Chakravarty, M.; Bhuvan Kumar, N. N.; Kumara Swamy, K. C. Cycloaddition Reactions of Allenylphosphonates and Related Allenes with Dialkyl Acetylenedicarboxylates, 1,3-Diphenylisobenzofuran, and Anthracene. J. Org. Chem. 2011, 76, 920–938. (e) Srinivas, V.; Sajna, K. V.; Kumara Swamy, K. C. To Stay as Allene or go Further? Synthesis of Novel Phosphono-Heterocycles and Polycyclics via Propargyl Alcohols. Chem. Commun. 2011, 47, 5629–5631. (f) Gangadhararao, G.; Kumara Swamy, K. C. Unusual Nitrogen based Heterocycles via Allenic Intermediates from the Reaction of Propargyl Alcohols with P(III) Substrates. Tetrahedron. 2014, 70, 2643–2653. (g) Kumara Swamy, K. C.; Mandala Anitha, M.; Gangadhararao, G.; Rama Suresh, R. Exploring Allene Chemistry using Phosphorusbased Allenes as Scaffolds. Pure Appl. Chem. 2017, 89, 367–368. (h) Bogachenkov, A. S.; Dogadina, A. V.; Boyarskaya, I. A.; Boyarskiy, V. P.; Vasilyev, A. V. Synthesis of 1,4-Dihydrophosphinoline 1-Oxides by Acid-Promoted Cyclization of 1-(Diphenylphosphoryl)Allenes. Org. Biomol. Chem. 2016, 1370–1381. (i) Lozovskiy, S. V.; Ivanov, A. Y.; Bogachenkov, A. S.; Vasilyev, A. V. 2,5-Dihydro-1,2-Oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles: Generation, NMR Study, and Reactions. Chem. Select. 2017, 2, 4505–4510. ((j) Mao, M.; Zhang, L.; Chen, Y.-Z.; Zhu, J.; Wu, L. Palladium-Catalyzed Coupling of Allenylphosphine Oxides with N-Tosylhydrazones toward Phosphinyl [3]Dendralenes. ACS Catal. 2017, 7, 181–186.
   PubMed Web of Science ®Google Scholar
• Ma, S. Electrophilic Addition and Cyclization Reactions of Allenes. Acc. Chem. Res. 2009, 42, 1679–1688.
   PubMed Web of Science ®Google Scholar
• Brel, V. K. Phosphonoallenes for Building Organophosphorus Derivatives. Heteroatom. Chem. 2006, 17, 547–556.
   Web of Science ®Google Scholar
• Angelov, C. M.; Christov, C. Z.; Ionin, B. I. Chlorination of Tertiary Allenic Phosphine Oxides. Zh. Obshch. Khim. 1982, 52, 264–267.
   Google Scholar
• Khusainova, N. G.; Naumova, L. V.; Berdnikov, E. A.; Pudovik, A. N. Interaction of Phosphorylated Allenes with Sulfenyl Chlorides. Zh. Obshch. Khim. 1982, 52, 1040–1046.
   Google Scholar
• Enchev, D. D.; Angelov, C. M.; Krawchik, E.; Skowronska, A.; Michalski, J. 2,5-Dihydro-1,2-Oxaphospholene Derivatives by the Reaction of 1,2-Alkadienephosphonates and Phosphorus Pseudohalogenes. Phosphorus Sulfur Silicon 1991, 57, 249–253.
   Web of Science ®Google Scholar
• Guo, H.; Qian, R.; Guo, Y.; Ma, S. Neighboring Group Participation of Phosphine Oxide Functionality in the Highly Regio- and Stereoselective Iodohydroxylation of 1,2-Allenylic Diphenyl Phosphine Oxides. J. Org. Chem. 2008, 73, 7934–7938.
   PubMed Web of Science ®Google Scholar
• He, G.; Fu, C.; Ma, S. Studies on Highly Regio- and Stereoselective Fluorohydroxylation Reaction of 3-Aryl-1,2-Allenyl Phosphine Oxides with Selectfluor. Tetrahedron 2009, 65, 8035–8042.
   Web of Science ®Google Scholar
• He, G.; Guo, H.; Qian, R.; Guo, Y.; Fu, C.; Ma, S. Studies on Highly Regio- and Stereoselective Selenohydroxylation Reaction of 1,2-Allenyl Phosphine Oxides with PhSeCl. Tetrahedron 2009, 65, 4877–4889.
   Web of Science ®Google Scholar
• (a) Brel, V. K. Synthesis and Cyclization of Diethylphosphono-Substituted α-Allenic Alcohols to 4-(Diethylphosphono)-2,5-Dihydrofurans. Synthesis. 1999, 463–466. (b) Brel, V. K. Synthesis and Intramolecular Cyclization of Diethylphosphono-Substituted Allenic Glycols. Synthesis. 2001, 1539–1545. (c) Brel, V. K.; Belsky, V. K.; Stash, A. I.; Zavodnik, V. E.; Stang, P. J. Synthesis and Molecular Structure of New Unsaturated Analogues of Nucleotides Containing Six-Membered Rings. Eur. J. Org. Chem. 2005, 512–521.
   Web of Science ®Google Scholar
• Brel, V. K.; Abramkin, E. V. Cyclization of Allenyl Phosphonates to 3-Chloro-4-(Diethylphosphono)-2,5-Dihydrofurans Induced by CuCl2. Mendeleev Commun. 2002, 12, 64–66.
   Web of Science ®Google Scholar
• (a) Jacobs, T. L.; Macomber, R.; Zucker, D. Addition Reactions of Allenes. III. 2,4-Dinitrobenzenesulfenyl Chloride and Bromine. J. Am. Chem. Soc. 1967, 89, 7001–7005. (b) Toda, F.; Komora, T.; Akagi, K. A New Bromoallene Alcohol. Its Isolation and Reaction. Bull. Chem. Soc. Jpn. 1968, 41, 1493. (c) Hoft, S.; Brandsma, L. Acid-Catalyzed Ring Rlosure of 1-Methoxy- or 1-Methylthio-1-(α- or β-Hydroxyalkyl)Allenes: Formation of 3,8-Dimethoxy-1,6-Dioxacyclodeca-3,8-Dienes and 4-Methylthio-5,6-Dihydro-2H-Pyrans. Recl. Trav. Chim. Pays. Bas. 1969, 88, 845–850. (d) Gelin, R.; Gelin, S.; Albrand, M. Isomerisation en milieu acide d'alcools α-alleniques. Bull. Soc. Chim. Fr. 1972, 720–723. (e) Gelin, R.; Gelin, S.; Albrand, M. Oxymercuration-demercuration d'alcools α-alleniques. Bull. Soc. Chim. Fr. 1972, 1946–1949. (f) Olsson, L. I.; Claesson, A. Synthesis of 2,5-Dihydrofurans and 5,6-Dihydro-2H-Pyrans by Silver(I)-Catalyzed Cyclization of Allenic Alcohols. Synthesis. 1979, 743–745. (g) Beaulieu, P. L.; Morisset, V. M.; Garratt, D. G. The Synthesis of 2,5-Dihydrofurans from α-Allenic Alcohols. Tetrahedron Lett. 1980, 21, 129–132. (h) Marshal, J. A.; Wang, X. [2,3]-Wittig Rearrangements of Nonracemic (Propargyloxy)Acetic Acids and Esters. Synthesis of Optically Active 2,5-Dihydrofurans. J. Org. Chem. 1990, 55, 2995–2996. (i) Marshal, J. A.; Wang, X. Synthesis of Enantioenriched α-Hydroxy-α-Allenylacetic Acids by [2,3]-Wittig Rearrangement of α-(Propargyloxy)Acetates. J. Org. Chem. 1991, 56, 4913–4918. (j) Marshal, J. A.; Pinney, K. G. Stereoselective Synthesis of 2,5-Dihydrofurans by Sequential SN2' Cleavage of Alkynyloxiranes and Silver(I)-Catalyzed Cyclization of the Allenylcarbinol Products. J. Org. Chem. 1993, 58, 7180–7184. (k) Ma, S.; Gao, W. Efficient Synthesis of 4-(2'-Alkenyl)-2,5-Dihydrofurans via PdCl2-Catalyzed Coupling-Cyclization Reaction of 2,3-Allenols with Allylic Halides. Tetrahedron Lett. 2000, 41, 8933–8936. (l) Krause, N.; Laux, M.; Hoffman-Roder, A. New Methods for the Stereoselective Synthesis of 2-Hydroxy-3,4-Dienoates and Functionalized 2,5-Dihydrofurans. Tetrahedron Lett. 2000, 41, 9613–9616. (m) Hoffman-Roder, A.; Krause, N. Gold(III) Chloride Catalyzed Cyclization of a-Hydroxyallenes to 2,5-Dihydrofurans. Org. Lett. 2001, 3, 2537–2538. (n) Krause, N.; Hoffman-Roder, A.; Canisius, J. From Amino Acids to Dihydrofurans: Functionalized Allenes in Modern Organic Synthesis. Synthesis. 2002, 1759–1774.
   Web of Science ®Google Scholar
• Ganguli, M.; Burka, L. T.; Harris, T. M. Structural Studies of the Mycotoxin Verrucosidin. J. Org. Chem. 1984, 49, 3762–3766.
   Web of Science ®Google Scholar
• Franck, B.; Gehrken, H. P. Citreoviridins from Aspergillus Terreus. Angew. Chem. Int. Ed. Engl. 1980, 19, 461–462.
   PubMed Web of Science ®Google Scholar
• Yamauchi, R.; Miyake, N.; Kato, K.; Ueno, Y. Peroxyl-Radical Reaction of Retinyl Acetate in Solution. Biosci. Biotechnol. Biochem 1992, 56, 1529–1532.
   PubMed Web of Science ®Google Scholar
• (a) Boivin, T. L. B. Synthetic Routes to Tetrahydrofuran, Tetrahydropyran, and Spiroketal Units of Polyether Antibiotics and a Survey of Spiroketals of Other Natural Products. Tetrahedron. 1987, 43, 3309–3362. (b) Koert, U.; Stein, M.; Wagner, H. Bidirectional and Convergent Routes to Oligo(Ttetrahydrofurans). Chem. Eur. J. 1997, 3, 1170–1180.
   Web of Science ®Google Scholar
• Perron, F.; Albizati, K. F. Chemistry of Spiroketals. Chem. Rev. 1989, 89, 1617–1661.
   Web of Science ®Google Scholar
• VanBrunt, M. P.; Standaert, R. F. A Short Total Synthesis of (+)-Furanomycin. Org. Lett. 2000, 2, 705–708.
   PubMed Web of Science ®Google Scholar
• (a) Ismailov, I. E.; Ivanov, I. K.; Christov, V. C. Bifunctionalized Allenes. Part XV. Synthesis of 2,5-Dihydro-1,2-Oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes. Molecules. 2014, 19, 11056–11076. (b) Christov, V. C.; Ismailov, I. E.; Ivanov, I. K. Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-Dihydrofurans by Coinage Metal-Catalyzed Cyclo-Isomerization of Phosphorylated α-Hydroxyallenes. Molecules. 2015, 20, 7263–7275.
   PubMed Web of Science ®Google Scholar
  (c) Christov, V. C.; Ismailov, I. E.; Ivanov, I. K. Bifunctionalized Allenes. Part XVII. Synthesis of 2,5-Dihydro-1,2-Oxaphospholes and 2-Phosphoryl-2,5-Dihydrofurans by Electrophilic Cyclization and Coinage Metal-Catalyzed Cycloisomerization of Phosphorylated 3-(β-Hydroxy) Allenes. Int. J. Rec. Sci. Res. 2015, 6, 4526–4537.
   Google Scholar
• (a) Ivanov, I. K.; Parushev, I. D.; Christov, V. Ch. Bifunctionalized Allenes. Part XII. Electrophilic Cyclization and Addition Reactions of 4-Sulfinylated and 4-Sulfonylated Allenecarboxylates. Phosphorus Sulfur Silicon. 2014, 189, 1503–1513. (b) Ivanov, I. K.; Parushev, I. D.; Christov, V. Ch. Bifunctionalized Allenes. Part XI. Competitive Electrophilic Cyclization and Addition Reactions of 4-Phosphorylated Allenecarboxylates. Heteroatom Chem. 2014, 25, 60–71.
   Web of Science ®Google Scholar
• Hasanov, H. H.; Ivanov, I. K.; Christov, V. C. Bifunctionalized Allenes, Part XIX: Synthesis, Electrophilic Cyclization/Addition, and Coinage Metal-Catalyzed Cycloisomerization of Phosphorylated 3-(β-Hydroxy)Allenes. Heteroatom Chem. 2017, 28, e21357.
   Web of Science ®Google Scholar
• Christov, V. Ch.; Hasanov, H. H; Ivanov, I. K. Bifunctionalized Allenes. Part XVIII. Synthesis of 2,5-Dihydro-1,2-Oxaphospholes and 2-Phosphoryl-2,5-Dihydrofurans by Electrophilic Cyclization and Coinage Metal-Catalyzed Cycloisomerization of Phosphorylated 3-(α-Hydroxy)Allenes. Global J. Pure Appl. Chem. Res. (GJPACR) 2015, 3, 20–36. (b) Hasanov, H. H; Ivanov, I. K.; Christov, V. Ch. Bifunctionalized Allenes. Part XX. A Novel Method for Regioselective Synthesis of Phosphorylated 3-(α-Hydroxyalkyl)Allenes. Bull. Chem. Commun. B 2017, 49, 25–32.
   Google Scholar
• Baldwin, J. E. Rules for Ring Closure. J. Chem. Soc. Chem. Commun. 1976, 734–736.
   Google Scholar