Diastereoselective Synthesis of γ-Butenolides Catalyzed by Potassium tert-Butoxide

REFERENCES

• For reviews, see (a) Shiina , I. In Modern Aldol Reactions ; R. Mahrwald (Ed.); Wiley-VCH : Weinheim , 2004 ; vol. 2 , pp. 105 – 166 ; (b) Mukaiyama , T. ; Matsuo , J.-I. In Modern Aldol Reactions ; R. Mahrwald (Ed.); Wiley-VCH : Weinheim , 2004 ; vol. 1 , pp. 127 – 160 ; (c) Carreira , E. M. In Comprehensive Asymmetric Catalysis I–III ; E. N. Jacobsen , A. Pfaltz , and H. Yamamoto (Eds.); Springer-Verlag : Berlin , Germany , 1999 ; vol. 3 , pp. 997 – 1065 . For a recent study of Mukaiyama aldol reaction, see (d) Curti , C. ; Ranieri , B. ; Battistini , L. ; Rassu , G. ; Zambrano , V. ; Pelosi , G. ; Casiraghi , G. ; Zanardi , F. Catalytic, asymmetric vinylogous Mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: How the diene heteroatom impacts stereocontrol. Adv. Synth. Catal. 2010, 352, 2011; (e) Frings , M. ; Goedert , D. ; Bolm , C. Enantioselective synthesis of highly functionalised amides by copper-catalysed vinylogous Mukaiyama aldol reaction. Chem. Commun. 2010, 46, 5497; (f) Yamaoka , M. ; Nakazaki , A. ; Kobayashi , S. Rate enhancement by water in a TiCl4-mediated stereoselective vinylogous Mukaiyama aldol reaction. Tetrahedron Lett. 2010, 51, 287; (g) Curti , C. ; Sartori , A. ; Battistini , L. ; Rassu , G. ; Burreddu , P. ; Zanardi , F. ; Casiraghi , G. Vicarious silylative Mukaiyama aldol reaction: A vinylogous extension. J. Org. Chem. 2008, 73(14), 5446; (h) Shinoyama , M. ; Shirokawa , S. ; Nakazaki , A. ; Kobayashi , S. A switch of facial selectivities using α-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction. Org. Lett. 2009, 11(6), 1277; (i) Simsek , S. ; Kalesse , M. Enantioselective synthesis of polyketide segments through vinylogous Mukaiyama aldol reactions. Tetrahedron Lett. 2009, 50(26), 3485.
   Google Scholar
• For reviews of vinylogous aldol reactions, see (a) Rassu , G. ; Zanardi , F. ; Battistini , L. ; Casiraghi , G. The vinylogous aldol addition of heterocyclic silyloxy dienes: Application in synthesis. Synlett. 1999, 1333; (b) Casiraghi , G. ; Zanardi , F. ; Appendino , G. ; Rassu , G. The vinylogous aldol reaction: A valuable, yet understated carbon–carbon bond-forming maneuver. Chem. Rev. 2000, 100, 1929; (c) Denmark , S. E. ; Heemstra Jr. , J. R. ; Beutner , G. L. Catalytic, enantioselective, vinylogous aldol reactions. Angew. Chem. Int. Ed. 2005, 44, 4682; (d) Kalesse , M. Recent advances in vinylogous aldol reactions and their applications in the syntheses of natural products. Top. Curr. Chem. 2005, 244, 43.
   Google Scholar
• For reviews on butenolide-containing natural products, see (a) Rodriguez , A. D. The natural products chemistry of West Indian gorgonian octocorals . Tetrahedron 1995 , 51 , 4571 ; (b) Alali , F. W. ; Liu , X. X. ; McLaughlin , J. L. Annonaceae acetogenin: Recent progress . J. Nat. Prod. 1999 , 62 , 504 ; (c) Hanson , J. R. Steroids: Reactions and partial synthesis . Nat. Prod. Rep. 2002 , 19 , 381 .
   PubMed Web of Science ®Google Scholar
• (a) Ferrié , S. ; Reymond , S. ; Capdevielle , P. ; Cossy , J. Concise total synthesis of (−)-Muricatacin and (−)-iso-Cladospolide B using chemoselective cross-metathesis . Synlett 2007 , 18 , 2891 ; (b) Sarma , K. D. ; Zhang , J. ; Curran , T. T. Novel synthons from mucochloric acid: The first use of α,β-dichloro-γ-butenolides and γ-butyrolactams for direct vinylogous aldol addition . J. Org. Chem. 2007 , 72 , 3311, and references therein.
   Google Scholar
• (a) Raders , S. M. ; Verkade , J. G. Catalysis of Mukaiyama aldol reactions by a tricyclic aluminum alkoxide Lewis acid . J. Org. Chem. 2009 , 74 , 5417 ; (b) Ollevier , T. ; Bouchard , J. E. ; Desyroy , V. Diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan catalyzed by bismuth briflate . J. Org. Chem. 2008 , 73 , 331 ; (c) Yadav , J. S. ; Subba Reddy , B. V. ; Narasimhulu , G. ; Satheesh , G. Iodine as a mild and efficient catalyst for the diastereoselective synthesis of d-silyloxy-c-lactones . Tetrahedron Lett. 2008 , 49 , 5683 ; (d) Acocella , M. R. ; De Rosa , M. ; Massa , A. ; Palombi , L. ; Villano , R. ; Scettri , A. Silicon tetrachloride in organic synthesis: New applications for the vinylogous aldol reaction . Tetrahedron 2005 , 61 , 4091 ; (e) Kong , K. ; Romo , D. Diastereoselective, vinylogous Mukaiyama aldol additions of silyloxy furans to cyclic ketones: Annulation of butenolides and γ-lactones . Org. Lett. 2006 , 8 , 2909 ; (f) López , C. S. ; Álvarez , R. ; Vaz , B. ; Faza , O. N. ; de Lera , A. R. Simple diastereoselectivity of the BF3 · OEt2-catalyzed vinylogous Mukaiyama aldol reaction of 2-(trimethylsiloxy)furans with aldehydes . J. Org. Chem. 2005 , 70 , 3654 ; (g) Palombi , L. ; Acocella , M. R. ; Celenta , N. ; Massa , A. ; Villano , R. ; Scettri , A. Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system . Tetrahedron: Asymmetry 2006 , 17 , 3300 .
   PubMed Web of Science ®Google Scholar
• For recent asymmetric vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy) furan, see (a) Zhu , N. ; Ma , B. C. ; Zhang , Y. ; Wang , W. Organocatalyzed highly enantioselective and anti-selective construction of γ-butenolides through vinylogous Mukaiyama aldol reaction . Adv. Synth. Catal. 2010 , 352 , 1291 ; (b) Szlosek , M. ; Figadère , B. Highly enatioselective aldol reaction with 2-(trimethylsilyloxy) furan: The first catalytic asymmetric autoinductive aldol reaction . Angew. Chem. Int. Ed. 2009 , 48 , 1799 ; (c) Frings , M. ; Atodiresei , I. ; Runsink , J. ; Raabe , G. ; Bolm , C. Catalyzed vinylogous Mukaiyama aldol reactions with controlled enantio- and diastereoselectivities . Chem. Eur. J. 2009 , 15 , 1566 ; (d) Fabra , M. J. ; Fraile , J. M. ; Herrerías , C. I. ; Lahoz , F. J. ; Mayoral , J. A. ; Pérez , I. Surface-enhanced stereoselectivity in Mukaiyama aldol reactions catalyzed by clay-supported bis(oxazoline)–copper complexes . Chem. Commun. 2008 , 5402 ; (e) Rosa , M. D. ; Citro , L. ; Soriente , A. The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds: Hydrogen-bond catalysis in γ-butenolides synthesis . Tetrahedron Lett. 2006 , 47 , 8507 ; (f) Nagao , H. ; Yamane , Y. ; Mukaiyama , T. Effective synthesis of 5-substituted butenolide derivatives by using cinchonidine-derived quaternary ammonium phenoxide catalyst . Chem. Lett. 2007 , 36 , 8 .
   Web of Science ®Google Scholar
• (a) Chintareddy , V. R. ; Wadhwa , K. ; Verkade , J. G. P(PhCH2NCH2CH2)3N catalysis of Mukaiyama aldol reactions of aliphatic, aromatic, and heterocyclic aldehydes and trifluoromethyl phenyl ketone . J. Org. Chem. 2009 , 74 , 8118, and references therein; (b) Hatano , M. ; Suzuki , S. ; Takagi , E. ; Ishihara , K. Highly efficient synthesis of functionalized tertiary alcohols catalyzed by potassium alkoxide–crown ether complexes . Tetrahedron Lett. 2009 , 50 , 3171 .
   Web of Science ®Google Scholar
• Cahard , D. ; Duhamel , L. ; Lecomte , S. ; Poirier , J.-M. Prenylation reaction performed with catalytically generated potassium prenal dienolate . Synlett 1998 , 1399 .
   Web of Science ®Google Scholar