Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 21
68
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Alkatrienyl Sulfoxides and Sulfones. V. Tandem Cyclization, Rearrangement, and Aromatization of 1‐ and 3‐Vinylallenyl Sulfoxides and Sulfones in Diels‐Alder Reaction

&
Pages 3963-3973 | Received 20 Jun 2004, Published online: 12 Jan 2011

References

  • Carruthers , W. 1990 . Cycloaddition Reactions in Organic Synthesis Oxford : Pergamon . For reviews on the Diels‐Alder reaction, see:
  • Oppolzer , W. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. , Fleming , I. and Paquette , L. A. Vol. 5 , 315 – 399 . Oxford : Pergamon .
  • Jurczak , J. , Bauer , T. C. and Chapuis , C. 1995 . Houben‐Weyl Edited by: Helmchen , G. , Hoffmann , R. W. , Mulzer , J. and Schaumann , E. Vol. E21c , 2735 – 2871 . 2905 – 2952 . Stuttgart : Thieme .
  • Craig , D. 1995 . Houben‐Weyl Edited by: Helmchen , G. , Hoffmann , R. W. , Mulzer , J. and Schaumann , E. Vol. E21c , 2872 – 2904 . Stuttgart : Thieme .
  • Lautens , M. , Klute , W. and Tam , W. 1996 . Transition Metal‐Mediated Cycloaddition Reactions . Chem. Rev. , 96 : 49 – 92 . [PUBMED] [INFOTRIEVE]
  • Patai , S. , ed. 1980 . The Chemistry of Ketenes, Allenes and Related Compounds New York : Wiley‐Interscience .
  • Hopf , H. 1982 . The Chemistry of the Allenes , [2 + 4] Cycloadditions of Allenes Edited by: Landor , S. R. 563 – 577 . London : Academic Press .
  • Schuster , H. F. and Coppolla , G. M. 1984 . Allenes in Organic Synthesis 89 – 104 . New York : Wiley .
  • 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:[CROSSREF]
  • 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 .
  • Cauwberghs , S. G. and De Clercq , P. J. 1988 . A novel approach to periplanone‐b involving an intramolecular Diels‐Alder reaction with furan‐diene and allene‐dienophile . Tetrahedron Lett. , 29 : 6501 – 6503 . [CROSSREF]
  • 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 .
  • 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 .
  • Metz , P. , Betels , S. and Fröhlich , R. 1993 . An enantioselective approach to 3.alpha.‐hydroxy‐15‐rippertene. Construction of the tetracyclic ring system . J. Am. Chem. Soc. , 115 : 12595 – 12596 .
  • 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 . [CROSSREF]
  • 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[CROSSREF]
  • 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:
  • Jones , E. R.H. , Lee , H. H. and Whiting , M. C. 1960 . Researches on acetylenic compounds. Part LXII. The preparation and some synthetical applications of penta‐1,2,4‐triene and penta‐1,2,‐dien‐4‐yne . J. Chem. Soc. , : 341 – 352 . For intermolecular Diels‐Alder reactions of vinylallenes, see:[CROSSREF]
  • Bertrand , M. , Grimaldi , J. and Waegell , B. 1968 . Diels‐Alder cycloadditions of vinyl‐ and propenyl‐allene to methyl vinyl ketone . J. Chem. Soc., Chem. Commun. , : 1141 – 1142 .
  • Bertrand , M. , Grimaldi , J. and Waegell , B. 1971 . Mecanisme de reaction et structure des derives formes par reaction de Diels‐Alder entre trienes‐1,2,4 et cetones α,β ethyleniques . Bull. Soc. Chim. Fr. , 108 : 962 – 973 .
  • Bross , H. , Schneider , R. and Hopf , H. 1979 . Alkyne und kumulene. XI Darstellung und eigenschaften von 1,2,4‐trans,6‐trans‐octatetraen . Tetrahedron Lett. , 20 : 2129 – 2132 . [CROSSREF]
  • Schneider , R. , Siegel , H. and Hopf , H. 1981 . Thermische und photochemische dimerisierung von 1,2,4‐pentatrien (vinylallen) (Alkine und Cumulene, XIV) . Liebigs Ann. Chem. , : 1812 – 1825 .
  • Yoshida , K. and Grieco , P. A. 1985 . Synthesis and reactivity of (E)‐4,6,7‐octatrienoic acid sodium salt in aqueous Diels‐Alder reaction . Chem. Lett. , : 155 – 158 .
  • 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 . [CROSSREF]
  • 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 .
  • Wang , K. K. , Andemichael , Y. W. and Dhumrongvaraporn , S. 1989 . Regioselective synthesis of highly substituted arylsilanes by the reaction of the trimethylsilyl‐substituted vinylallenones with enamines . Tetrahedron Lett. , 30 : 1311 – 1314 . [CROSSREF]
  • 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 .
  • Dennehy , R. D. and Whitby , R. J. 1992 . Synthesis of Allenylketenimines via Titanocene vinylidene Complexes . J. Chem. Soc., Chem Commun. , : 35 – 36 . [CROSSREF]
  • 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. Heterocyclic Chem. , 31 : 871 – 876 .
  • 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 .
  • 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 . [CROSSREF]
  • 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 . [CROSSREF]
  • 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:
  • Deutsch , E. A. and Snider , B. B. 1983 . Synthesis of the hexahydronaphthalene moiety of (+)‐mevinolin . Tetrahedron Lett. , 24 : 3701 – 3704 . [CROSSREF]
  • 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 .
  • Okamura , W. H. 1983 . Pericyclic reactions of vinylallenes: from calciferols to retinoids and drimanes . Acc. Chem. Res. , 16 : 81 – 88 . [CSA]
  • Keck , G. E. and Kachensky , D. F. 1986 . A highly convergent total synthesis of (+)‐compactin . J. Org. Chem. , 51 : 2487 – 2493 .
  • Reich , H. J. , Eisenhart , E. K. , Olson , R. R. and Kelly , M. J. 1986 . Silyl ketone chemistry. Preparation and reactions of silyl allenol ethers. Diels‐Alder reaction of siloxy vinylallenes leading to sesquiterpenes . J. Am. Chem. Soc. , 108 : 7791 – 7800 .
  • 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 .
  • Schlindwein , H.‐J. and Himbert , G. 1989 . Einfluss von methyl‐ und phenyl‐gruppen in der allenischen ω‐possition auf die thermisch induzierten isomerisierungen von N‐[2‐furanyl‐(thienyl‐, pyrronyl‐)‐methyl]allencarboxamiden . Chem. Ber. , 122 : 2331 – 2339 .
  • Okamura , W. H. and Curtin , M. L. 1990 . Pericyclization of vinylallenes in organic chemistry: on the intramolecular Diels‐Alder reaction . Synlett , 1 : 1 – 9 . [CROSSREF]
  • 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 .
  • Mandai , T. , Ogawa , M. , Yamaoki , H. , Nakata , T. , Kawada , M. and Tsuji , J. 1991 . Palladium‐catalyzed reactions of 2‐alkynyl carbonates with olefins. A new synthetic method for vinyl allenes . Tetrahedron Lett. , 32 : 3397 – 3398 . [CROSSREF]
  • 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 . [CROSSREF]
  • Krause , N. 1993 . Synthesis of (±)‐sterpurene and hydroxylated derivates by 1,6‐addition of organocuprates to acceptor‐substituted enynes . Liebigs Ann. Chem. , : 521 – 525 .
  • Wender , P. A. , Jenkins , T. E. and Suzuki , S. 1995 . transition metal‐catalyzed intramolecular [4 + 2] diene‐allene cycloadditions: a convenient synthesis of angularly substituted ring systems with provision for catalyst‐controlled chemo‐ and stereocomplementarity . J. Am. Chem. Soc. , 117 : 1843 – 1844 .
  • 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 . [CROSSREF]
  • Klaboe , P. , Torgrimsen , T. , Christensen , D. H. , Hopg , H. , Eriksson , A. , Hagen , G. and Cyvin , S. J. 1974 . Spectrochimica Acta , 30A : 1527 – 1543 . For conformational analysis of vinylallenes, see:
  • Traetteberg , M. , Bakken , P. and Hopf , H. 1980 . Acta Chem. Scand. , A34 : 461 – 467 .
  • Bond , D. 1990 . An ab initio study of vinylallene conformations . J. Org. Chem. , 55 : 661 – 665 .
  • Christov , V. Ch. and Ivanov , I. K. 2002 . Alkatrienyl sulfoxides and sulfones. Part I. 3‐Methyl‐1,2,4‐pentatrienyl phenyl sulfoxide‐synthesis and electrophile‐induced cyclization reactions . Phosphorus, Sulfur, Silicon , 177 : 2445 – 2454 . Part I, see:[CROSSREF]
  • Christov , V. Ch. and Ivanov , I. K. 2002 . Alkatrienyl sulfoxides and sulfones. Part II. (5‐Methyl‐1,3,4‐hexatriene‐3‐yl) phenyl sulfoxide‐synthesis and electrophile‐promoted cyclization reactions . Sulfur Lett. , 25 : 191 – 198 . Part II, see:[CROSSREF]
  • Christov , V. Ch. and Ivanov , I. K. 2003 . Alkatrienyl sulfoxides and sulfones. Part III. 5‐Methyl‐3‐(methylsulfonyl)hexa‐1,3,4‐triene – synthesis and electrophile‐induced cyclization reactions . Heterocyclic Commun. , 9 : 629 Part III, see:
  • Christov , V. Ch. and Ivanov , I. K. 2004 . Alkatrienyl sulfoxides and sulfones. Part IV. Synthesis and electrophile‐induced cyclization reactions of 3‐methyl‐1‐methylsulfonylpenta‐1,2,4‐triene . Phosphorus, Sulfur, Silicon , in press For Part IV, see:
  • 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 . [CROSSREF]
  • 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 .
  • 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 .
  • 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 .
  • See Ref.6a 6b 6c 6d 6e 6f 6g 6h 6i 6j 6k 6l 6m 6n 6o
  • See Ref.8d

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.