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Regioselective and Asymmetric Diels−Alder Reaction of 1- and 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated Chiral Oxazaborolidine
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Section:Abstract
Cationic oxazaborolidine 2 affords Diels−Alder adducts of ethyl acrylate and 2-substituted cyclopentadienes, derived from the corresponding mixture of regioisomers, as single isomers in excellent yields and enantioselectivities. Furthermore, Diels−Alder adducts of 1-substituted cyclopentadienes are obtained through a one-pot procedure whereby ethyl acrylate is initially employed to consume all 2-substituted cyclopentadiene. Subsequently, various 2,5-disubstituted benzoquinones are added to react with remaining 1-substituted cyclopentadiene. Remarkably, reaction occurs selectively at the double bond coordinated anti to catalyst 2 to provide adducts containing adjacent all-carbon quaternary stereocenters in high yields and excellent enantioselectivities.
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
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Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels−Alder Reaction
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[4 + 2] Cycloaddition Reactions Catalyzed by a Chiral Oxazaborolidinium Cation. Reaction Rates and Diastereo-, Regio-, and Enantioselectivity Depend on Whether Both Bonds Are Formed Simultaneously
Santanu Mukherjee and E. J. CoreyOrganic Letters2010 12 (5), 1024-1027[4 + 2] Cycloaddition Reactions Catalyzed by a Chiral Oxazaborolidinium Cation. Reaction Rates and Diastereo-, Regio-, and Enantioselectivity Depend on Whether Both Bonds Are Formed Simultaneously
Santanu Mukherjee and E. J. CoreyOrganic Letters2010 12 (5), 1024-1027The reaction rates and products in enantioselective Diels−Alder reactions with a range of dienophiles correlate with the expected degree of concertedness of bond formation in the transition state.
(1R)-(+)-Camphor and Acetone Derived α′-Hydroxy Enones in Asymmetric Diels−Alder Reaction: Catalytic Activation by Lewis and Brønsted Acids, Substrate Scope, Applications in Syntheses, and Mechanistic Studies
Patricia Bañuelos, Jesús M. García, Enrique Gómez-Bengoa, Ada Herrero, José M. Odriozola, Mikel Oiarbide, Claudio Palomo and Jesús RazkinThe Journal of Organic Chemistry2010 75 (5), 1458-1473(1R)-(+)-Camphor and Acetone Derived α′-Hydroxy Enones in Asymmetric Diels−Alder Reaction: Catalytic Activation by Lewis and Brønsted Acids, Substrate Scope, Applications in Syntheses, and Mechanistic Studies
Patricia Bañuelos, Jesús M. García, Enrique Gómez-Bengoa, Ada Herrero, José M. Odriozola, Mikel Oiarbide, Claudio Palomo and Jesús RazkinThe Journal of Organic Chemistry2010 75 (5), 1458-1473The Diels−Alder reaction constitutes one of the most powerful and convergent C−C bond-forming transformations and continues to be the privileged route to access cyclohexene substructures, which are widespread within natural products and bioactive ...
Highly Enantioselective Diels−Alder Reactions of Maleimides Catalyzed by Activated Chiral Oxazaborolidines
Santanu Mukherjee and E. J. CoreyOrganic Letters2010 12 (3), 632-635Highly Enantioselective Diels−Alder Reactions of Maleimides Catalyzed by Activated Chiral Oxazaborolidines
Santanu Mukherjee and E. J. CoreyOrganic Letters2010 12 (3), 632-635Diels−Alder reactions of various combinations of maleimides and 1,3-dienes with cationic oxazaborolidines as catalysts have been shown to be highly efficient and enantioselective.
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- Published In Issue August 08, 2007
- Received May 23, 2007
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