Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 3
196
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Wittig Olefination–Claisen Rearrangement Protocol for Cyclohexene Annulation

, , , , , , , & show all
Pages 423-433 | Received 19 Jan 2009, Published online: 06 Jan 2010

REFERENCES

  • (a) Lohay , B. B. ; Zimbiniski , R. Silicon directed distereoselective and enantioselective Mukaiyama–Michael tandem aldol condensation: A novel strategy for six-membered ring cyclization . Tetrahedron Lett. 1990 , 50 , 7273 ; (b) Xu , K. ; Lalic , G. ; Sheehan , S. M. ; Shair , M. D. Dynamic kinetic resolution during a cascade reaction on substrates with chrial all-carbon quaternary centers . Angew. Chem. Int. Ed. 2005 , 44 , 2259 ; (c) Shindo , M. ; Sato , Y. ; Shishido , K. A novel tandem [2 + 2] cycloaddition–Dieckmann condensation: Facile one-pot process to obtain 2,3-disubstituted-2-cycloalkenones from ynolates . J. Am. Chem. Soc. 1999 , 121 , 6507 ; (d) Wada , A. ; Sawada , K. ; Ono , N. ; Ito , M. Isocyclic compounds retinoids and related compounds, part 27: An improved synthesis of benzocycloalkanone derivatives . Chem. Pharm. Bull. 2004 , 52 , 132 ; (e) Posner , G. H. ; Shulman-Roskes , E. M. A one-flask multicomponent annulation reaction as the key step in a total synthesis of spirobicyclic (±)-β-vetivone . Tetrahedron 1992 , 48 , 4677 .
  • (a) Rao , H. S. ; Jothilingam , S. Solvent-free microwave-mediated Michael addition reactions . J. Chem. Sci. 2005 , 117 , 323 ; (b) Snider , B. B. ; Shi , B. A novel extension of the Stork–Jung vinylsilane Robinson annelation procedure for the introduction of the cyclohexene of guanacastepene . Tetrahedron Lett. 2001 , 42 , 9123 ; (c) Abad , A. ; Agullo , C. ; Arno , M. ; Cunat , A. C. ; Garcia , M. T. ; Zaragoza , R. J. Enantioselective synthesis of cuparane sesquiterpenes: Synthesis of (–)cuparene and (–)-δ-cuparenol . J. Org. Chem. 1996 , 61 , 5916 ; (d) Cheeseman , E. N. Synthesis of 4,4-bis(2-methoxyethyl)cyclohexanone and of 4,4-bis(2-methoxyethyl)-2-cyclohexen-1-one . Org. Prep. Proced. Int. 1990 , 22 , 519 ; (e) Takahashi , S. ; Oritani , T. ; Yamashita , K. Total synthesis of (+)-methyl trisporate b, fungal sex hormone . Agric. Biol. Chem. 1987 , 51 , 1143 ; (f) Banerjee , A. K. ; Nasipuri , D. ; Pakrashi , S. C. A simple and highly stereoselective route to (+)-podocarpic acid . J. Org. Chem. 1990 , 55 , 3952 ; (g) Krow , G. R. ; Carmosin , R. ; Mancuso , A. A simple synthesis of 4-cyclohexene-1,2-cis-diol and its use as the precursor of a functionalized cyclohexenone synthon . Org. Prep. Proced. Int. 1977 , 9 , 285 .
  • (a) Fringuelli , F. ; Girotti , R. ; Pizzo , F. ; Vaccaro , L. [AlCl3 + 2THF]: A new and efficient catalytic system for Diels–Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions . Org. Lett. 2006 , 8 , 2487 ; (b) Yeung , Y.-Y. ; Hong , S. ; Corey , E. J. A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor oseltamivir from 1,3-butadiene and acrylic acid . J. Am. Chem. Soc. 2006 , 128 , 6310 ; (c) Proteau , P. J. ; Hopkins , P. B. Sulfur directed Diels–Alder reactions: Synthesis of 1,5-disubstituted cyclohexene derivatives . J. Org. Chem. 1985 , 50 , 141 ; (d) Snowden , R. L. ; Linder , S. M. ; Wüst , M. A regioselective cyclohexannulation procedure via dienamine [4 + 2] cycloaddition: Synthesis of functionalized decalins . Helv. Chim. Acta 1989 , 72 , 892 ; (e) Ohno , M. ; Mori , K. ; Eguchi , S. Site selective cycloaddition reaction of 1-methoxy-1-trimethylsiloxy-1,3,5-hexatriene with dienophile . Tetrahedron Lett. 1986 , 27 , 3381 ; (f) Jung , M. E. ; Ho , D. ; Chu , H. V. Selective synthesis of highly substituted cyclohexenes via mixed Lewis acid–catalyzed Diels–Alder reactions of highly substituted dienes and dienophiles . Org. Lett. 2005 , 7 , 1649 .
  • (a) Ferrier , R. J. Unsaturated carbohydrates, part 21: A carbocyclic ring closure of a hex-5-enopyranoside derivative. J. Chem. Soc., Perkin Trans 1 1979, 1455; (b) Ferrier , R. J. ; Middleton , S. The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes. Chem. Rev. 1993, 93, 2779. For recent applications of carbocyclization, see (c) Tanimoto , H. ; Kato , T. ; Chida , N. Total synthesis of (+)-galanthamine starting from d-glucose. Tetrahedron Lett. 2007, 48, 6267; (d) Bohno , M. ; Sugie , K. ; Imase , H. ; Yusof , Y. B. ; Oishi , T. ; Chida , N. Total synthesis of amaryllidaceae alkaloids, (+)-vittatine and (+)-haemanthamine, starting from d-glucose. Tetrahedron 2007, 63, 6977.
  • Berezin , I. V. ; Vartanyan , L. S. ; Kazanskaya , N. F. Synthesis of cyclohexanone and cyclohexanol containing carbon-14 in the functional group . Vestnik Moskoyskogo Universiteta 1956 , 11 ( 2 ).
  • (a) Büchi , G. ; Powell , J. E. The Claisen rearrangement of 3,4-dihydro-2H-pyranylethylenes: A new method for the synthesis of cyclohexenes . J. Am. Chem. Soc. 1970 , 92 , 3126 ; (b) Büchi , G. ; Powell , J. E. Structurally selective method for the preparation of certain Diels–Alder adducts . J. Am. Chem. Soc. 1967 , 89 , 4559 .
  • (a) Taber , D. F. ; Kanai , K. ; Jiang , Q. ; Bui , G. Enantiomerically pure cyclohexenones by Fe-mediated carbonylation of alkenyl cyclopropanes . J. Am. Chem. Soc. 2000 , 122 , 6807 ; (b) Grossman , R. B. ; Pendharkar , D. S. ; Rasne , R. M. ; Melissa , A. V. Double annulation route to highly substituted and functionalized cis bicyclic and tricyclic δ-lactams and imides . J. Org. Chem. 2000 , 65 , 3255 ; (c) Grossman , R. B. ; Pendharkar , D. S. ; Brian , O. P. [n + 1] annulation route to highly substituted cyclic ketones with pendant ketone, nitrile, and ester functionality . J. Org. Chem. 1999 , 64 , 7178 .
  • ElDouhaibi , A. S. ; Lozanov , M. ; Montgomery , J. A multicomponent approach to substituted benzenes involving sequential nickel-catalyzed reactions . Tetrahedron 2006 , 62 , 11460 .
  • Kopach , M. E. ; Kolis , S. P. ; Liu , R. ; Robertson , J. W. ; Chordia , M. D. ; Harman , W. D. Stereodefined tandem addition reactions of η 2-arenes: A versatile route to functionalized cyclohexenes . J. Am. Chem. Soc. 1998 , 120 , 6199 .
  • (a) Maudru , E. ; Singh , G. ; Wightman , R. H. Radical cyclization of carbohydrate alkynes: Synthesis of highly functionalized cyclohexenes and carbasugars . Chem. Commun. 1998 , 15 , 1505 ; (b) Kim , K. ; Okamoto , S. ; Sato , F. Regiocontrol of radical cyclization by Lewis acids: Efficient synthesis of optically active functionalized cyclopentanes and cyclohexanes . Org. Lett. 2001 , 3 , 67 .
  • (a) Enders , D. ; Hüttl , R. M. ; Runsink , J. ; Gerhard Raabe , G. ; Wendt , B. Organocatalytic one-pot asymmetric synthesis of functionalized tricyclic carbon frameworks from a triple-cascade/Diels–Alder sequence . Angew. Chem. Int. Ed. 2007 , 46 , 467 ; (b) Heber , D. ; Stoyanov , E. V. Synthesis of functionalized 4H-pyran and cyclohexanone derivatives via three-component reactions of dimethyl acetonedicarboxylate, aromatic aldehydes, and malanonitrile . Synthesis 2003 , 2 , 227 ; (c) Ishii , A. ; Furasawa , K. ; Omata , T. ; Nakayama , J. Reactions of sterically congested 1,6- and 1,7-bis(diazo)alkanes with elemental sulfur and selenium: Formation of cyclohexene, 1,2-dithiocane, 1,2-diselenocane, and 1,2,3-triselenecane derivatives . Heteroat. Chem. 2002 , 13 , 351 .
  • Myers , A. G. ; Siegel , D. R. ; Buzard , D. J. ; Charest , M. G. Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions . Org. Lett. 2001 , 3 , 2923 .
  • Schneider , C. ; Reese , O. Domino Michael aldol and domino Michael–Mannich reactions: Highly stereoselective synthesis of functionalized cyclohexanes . Angew. Chem. Int. Ed. 2000 , 39 , 2948 .
  • Kitano , H. ; Minami , S. ; Morita , T. ; Matsumoto , K. ; Hatanaka , M. Annulation of 2-oxoalkylidenephenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones . Synthesis 2002 , 6 , 739 .
  • (a) Carlone , A. ; Marigo , M. ; North , C. ; Landa , A. ; J⊘rgensen , K. A. A simple asymmetric organocatalytic approach to optically active cyclohexenones. Chem. Commun. 2006, 4928; (b) J⊘rgensen , K. A. ; Reyes , E. ; Jiang , H. ; Milelli , A. ; Elsner , P. ; Hazell , R. G. How to make five contiguous stereocenters in one reaction: Asymmetric organocatalytic synthesis of pentasubstituted cyclohexanes. Angew. Chem. Int. Ed. 2007, 46, 9202.
  • (a) Hyldtoft , L. ; Madsen , R. Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis . J. Am. Chem. Soc. 2000 , 122 , 8444 ; (b) Martin , E. M. Synthesis of medium-sized rings by the ring-closing metathesis reaction . Angew. Chem. Int. Ed. 2000 , 39 , 2073 ; (c) Schrock , R. R. Olefin metathesis by molybdenum imido alkylidene catalysts . Tetrahedron 1999 , 55 , 8141 ; (d) Grubbs , R. H. ; Miller , S. J. ; Fu , G. C. Ring-closing metathesis and related process in organic synthesis . Acc. Chem. Res. 1995 , 28 , 446 .
  • Kulkarni , M. G. ; Pendharkar , D. S. ; Rasne , R. M. Wittig olefination: An efficient route for the preparation of allyl vinyl ether precursors for the Claisen rearrangement . Tetrahedron Lett. 1997 , 38 , 1459 .
  • Kulkarni , M. G. ; Davawala , S. I. ; Doke , A. K. ; Pendharkar , D. S. An expedient protocol for cyclopentenone annulation . Synthesis 2004 , 2919 .

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.