Alkatrienyl Sulfoxides and Sulfones, VIII: Diels–Alder Reaction of 3‐Methylpenta‐1,2,4‐trienyl Phenyl Sulfoxide with Maleic Anhydride

References

• Carruthers , W. 1990 . Cycloaddition Reactions in Organic Synthesis Oxford : Pergamon . (For reviews on the Diels–Alder reaction, see)
   Google Scholar
• Oppolzer , W. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. , Fleming , I. and Paquette , L. A. Vol. 5 , 315 – 399 . Oxford : Pergamon .
   Google Scholar
• Jurczak , J. , Bauer , T. and Chapuis , C. 1995 . Houben‐Weyl, Methods of Organic Synthesis, Vol. E21c, Steroselective Synthesis, 1.6.1 Cycloadditions Edited by: Helmchen , G. , Hoffmann , R.W. , Mulzer , J. and Schaumann , E. 2735 – 2871 . Stuttgart : Thieme .
   Google Scholar
• Craig , D. 1995 . Houben‐Weyl, Methods of Organic Synthesis, Vol. E21c, Steroselective Synthesis, 1.6.1 Cycloadditions Edited by: Helmchen , G. , Hoffmann , R.W. , Mulzer , J. and Schaumann , E. Vol. E21c , 2872 – 2904 . Stuttgart : Thieme .
   Google Scholar
• Lautens , M. , Klute , W. and Tam , W. 1996 . Transition metal–mediated cycloaddition reactions . Chem. Rev. , 96 : 49 – 92 .
   PubMedGoogle Scholar
• Patai , S. , ed. 1980 . Allenes and Related Compounds New York : Wiley‐Interscience . The Chemistry of Ketenes
   Google Scholar
• Hopf , H. 1982 . “ [2+4] Cycloadditions of allenes ” . In The Chemistry of the Allenes Edited by: Landor , S. R. 563 – 577 . London : Academic Press .
   Google Scholar
• Schuster , H. F. and Coppolla , G. M. 1984 . Allenes in Organic Synthesis 89 – 104 . New York : Wiley .
   Google Scholar
• Ma , S. 2005 . Some typical advances in the synthetic applications of allenes . Chem. Rev. , 105 : 2829 – 2871 .
   PubMed Web of Science ®Google Scholar
• Fink , M. , Gaier , H. and Gerlach , H. 1982 . 2,3‐Alkadiensäureester als Dienophile; Anwendung bei der Synthese von (+)‐(R)‐Lasiodiplodin . Helv. Chim. Acta , 65 : 2563 – 2569 . (For Diels–Alder reactions wherein allenes are used as dienophiles, see)
   Google Scholar
• Hayakawa , K. , Nishiyama , H. and Kanematsu , K. 1985 . Reagent design and study of allene as a promising class of reagents (synthons) for cycloaddition: The site‐selective and regioselective Diels–Alder reactions of (phenylsulfonyl)propadiene and alkylation of the adducts . J. Org. Chem. , 50 : 512 – 517 .
   Google Scholar
• Block , E. and Putman , D. 1990 . Allenyl chloromethyl sulfones, new dienophile‐diene synthons: A simple iterative ring‐growing procedure . J. Am. Chem. Soc. , 112 : 4072 – 4074 .
   Web of Science ®Google Scholar
• Padwa , A. , Bullock , W. H. , Norman , B. H. and Perumattam , J. 1991 . (Nitroaryl)sulfinyl‐substituted allenes. Novel and convenient propargyl alcohol synthons in 4+2 cycloaddition chemistry . J. Org. Chem. , 56 : 4252 – 4259 .
   Google Scholar
• Ikeda , I. , Honda , K. , Osawa , E. , Shiro , M. , Aso , M. and Kanematsu , K. 1996 . Structure and asymmetric Diels–Alder reactions of optically active allene‐1,3‐dicarboxylates . J. Org. Chem. , 61 : 2031 – 2037 .
   Google Scholar
• Murakami , M. , Itami , K. and Ito , Y. 1997 . Directed intermolecular [4+2] cycloaddition of unactivated 1,3‐diene substrates with high regio‐and stereoselectivities . J. Am. Chem. Soc. , 119 : 7163 – 7164 . and references cited therein
   Google Scholar
• Egenburg , I. Z. 1978 . Methods of synthesis and properties of conjugated eneallenic hydrocarbons . Russ. Chem. Rev. , 47 : 470 – 501 . (For a review on the chemistry of vinylallenes, see)
   Google Scholar
• Angelov , C. M. , Mondeshka , D. M. and Tancheva , C. N. 1985 . Spontaneous aromatization of Diels–Alder adducts in the reaction of alkatrienylphosphonates with dialkyl esters of acetylenedicarboxylic acid . J. Chem. Soc., Chem. Commun. , : 647 – 648 .
   Google Scholar
• Reich , H. J. , Eisenhart , E. K. , Whipple , W. L. and Kelly , M. J. 1988 . Stereochemistry of vinylallene cycloadditions . J. Am. Chem. Soc. , 110 : 6432 – 6442 .
   Google Scholar
• Mondeshka , D. M. , Tancheva , C. N. and Angelov , C. M. 1990 . 1,5‐Sigmatrope umlagerung von Diels–Alder addukten bei der reaction von alkatrienphosphonaten mit acetylencarbonsaureestern—Ein neuer weg zur synthese von benzyl‐ und phenylphosphonaten . Chem. Ber. , 123 : 1381 – 1386 .
   Google Scholar
• Wang , X. , Donovalova , J. , Hollis , A. , Johnson , D. , Rodrigues , A. , Kennedy , G. D. , Krishnan , G. and Banks , H. 1994 . Diels–Alder reactivity of vinylsulfoxyallenes . J. Heterocycl. Chem. , 31 : 871 – 876 .
   Google Scholar
• Koop , U. , Handke , G. and Krause , N. 1996 . Synthesis of vinylallenes by conjugate 1,6‐, 1,8‐, 1,10‐and 1,12‐addition reactions of organocuprates with acetylenic Michael acceptors and their use as dienes in intermolecular Diels–Alder reactions . Liebigs Ann. Chem , : 1487 – 1499 .
   Google Scholar
• Murakami , M. , Ubukata , M. , Itami , K. and Ito , Y. 1998 . Rhodium‐catalyzed intermolecular [4+2] cycloaddition of unactivated substrates . Angew. Chem. Int. Ed. Engl. , 37 : 2248 – 2250 .
   Google Scholar
• Spino , C. , Thibault , C. and Gingras , S. 1998 . Stereoselective construction of tetrasubstituted exocyclic alkenes from the [4+2]‐cycloaddition of vinylallenes . J. Org. Chem. , 63 : 5283 – 5287 .
   Google Scholar
• Deutsch , E. A. and Snider , B. B. 1982 . Synthesis of the hexahydronaphthalene moiety of (±)‐compactin (ML‐236B) . J. Org. Chem. , 47 : 2682 – 2684 . (For intramolecular Diels‐Alder reactions of vinylallenes, see)
   Web of Science ®Google Scholar
• Snider , B. B. and Burbaum , B. W. 1983 . Intramolecular Diels–Alder reactions of alkenylallenes: A model study for the bottom half of chlorothricolide . J. Org. Chem. , 48 : 4370 – 4374 .
   Google Scholar
• Okamura , W. H. 1983 . Pericyclic reactions of vinylallenes: From calciferols to retinoids and drimanes . Acc. Chem. Res. , 16 : 81 – 88 .
   Web of Science ®Google Scholar
• Gibbs , R. A. , Bartels , K. , Lee , R. W. K. and Okamura , W. H. 1989 . An enantioselective central axial–central chiral element transfer process leading to a concise synthesis of (+)‐sterpurene: Intramolecular Diels–Alder reactions of vinylallene sulfoxides . J. Am. Chem. Soc. , 111 : 3717 – 3725 .
   Google Scholar
• Okamura , W. H. and Curtin , M. L. 1990 . Pericyclization of vinylallenes in organic chemistry . On the intramolecular Diels–Alder reaction. Synlett , 1 : 1 – 9 .
   Google Scholar
• Curtin , M. L. and Okamura , W. H. 1990 . Synthetic and kinetic studies of the intramolecular Diels–Alder reactions of cycloalkenylallenylphosphine oxides . J. Org. Chem. , 55 : 5278 – 5287 .
   Google Scholar
• Dulcere , J. P. , Agati , V. and Faure , R. 1993 . Diels‐Alder intramolecular cycloaddition of vinylallenyl cycloalken‐3‐yl ethers . J. Chem. Soc., Chem. Commun. , : 270 – 271 .
   Google Scholar
• Regás , D. , Ruiz , J. M. , Afonso , M. M. , Galindo , A. and Palenzuela , J. A. 2003 . Intramolecular hetero Diels–Alder reactions of vinyl allenes and aldehydes . Tetrahedron Lett. , 44 : 8471 – 8474 .
   Google Scholar
• Klaboe , P. , Torgrimsen , T. , Christensen , D. H. , Hopg , H. , Eriksson , A. , Hagen , G. and Cyvin , S. 1974 . J. Spectrochimica Acta , 30A : 1527 – 1543 . (For conformational analysis of vinylallenes, see)
   Google Scholar
• Traetteberg , M. , Bakken , P. and Hopf , H. 1980 . Acta Chem. Scand. , A34 : 461 – 467 .
   Google Scholar
• Bond , D. 1990 . An ab initio study of vinylallene conformations . J. Org. Chem. , 55 : 661 – 665 .
   Google Scholar
• van Kruchten , E. M. G. A. and Okamura , W. H. 1982 . On the [2,3]‐sigmatropic rearrangements of sulfenate esters derived from alkenynols: Synthesis of vinylallene and vinylacetylene sulfoxides . Tetrahedron Lett. , 23 : 1019 – 1022 .
   Web of Science ®Google Scholar
• Reischl , W. and Okamura , W. H. 1982 . Electrocyclization of 1‐allenyldienes: Novel synthesis of drimatrienes and related trans‐decalins . J. Am. Chem. Soc. , 104 : 6115 – 6117 .
   Web of Science ®Google Scholar
• Okamura , W. H. , Peter , R. and Reischl , W. 1985 . Allenyldiene electrocyclization, a stereospecific tandem center‐axis‐center chirality transfer: Synthesis of drimatrienes and related trans‐decalins . J. Am. Chem. Soc. , 107 : 1034 – 1041 .
   Google Scholar
• Okamura , W. H. , Shen , G.‐Y. and Tapia , R. 1986 . Sulfoxide‐induced acceleration and enhancement of geometric selectivity of a [1,5]‐sigmatropic hydrogen shift . J. Am. Chem. Soc. , 108 : 5018 – 5019 .
   Web of Science ®Google Scholar
• see Ref. 4
   Google Scholar
• see Ref. 6c
   Google Scholar
• Christov , V. C. and Ivanov , I. K. 2002 . 3‐Methyl‐1,2,4‐pentatrienyl phenyl sulfoxide—Synthesis and electrophile‐induced cyclization reactions . Phosphorus, Sulfur Silicon Relat. Elem. , 177 : 2445 – 2454 .
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. 2002 . (5‐Methyl‐1,3,4‐hexatriene‐3‐yl) phenyl sulfoxide—Synthesis and electrophile‐promoted cyclization reactions . Sulfur Lett. , 25 : 191 – 198 . for Part II, see
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. 2003 . 5‐Methyl‐3‐(methylsulfonyl)hexa‐1,3,4‐triene—synthesis and electrophile‐induced cyclization reactions . Heterocycl. Commun. , 9 : 629 – 634 . for Part III, see
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. 2004 . Synthesis and electrophile‐induced cyclization reactions of 3‐methyl‐1‐methylsulfonylpenta‐1,2,4‐triene . Phosphorus, Sulfur Silicon Relat. Elem. , 179 : 1681 – 1690 . for Part IV, see
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. 2004 . Tandem cyclization, rearrangement and aromatization of 1‐and 3‐vinylallenyl sulfoxides and sulfones in Diels–Alder reaction with dimethyl but‐2‐ynedioate . Synth. Commun. , 34 : 3963 – 3973 . for Part V, see
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. 2004 . Cheletropic addition of sulfur dioxide to 1‐and 3‐vinylallenyl sulfoxides and sulfones . Heterocycles , 63 : 2203 – 2206 . for Part VI, see
   Web of Science ®Google Scholar
• Christov , V. C. and Ivanov , I. K. Alkatrienyl sulfoxides and sulfones, part VII: Synthetic innovations of cycloaddition reactions of S‐functionalized vinylallenes . In Proceeding of the Balkan Conference of Young Scientists . Vol. 5 , pp. 230 – 235 . for Part VII, see
   Google Scholar