Direct Asymmetric Allylic Alkylation of Butenolides with Morita−Baylis−Hillman Carbonates
Organic Letters2010Vol. 12(4), pp. 720–723
Citations Over TimeTop 1% of 2010 papers
Abstract
The direct asymmetric allylic alkylation of beta,gamma-butenolides with MBH carbonates to access gamma,gamma-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers has been presented in excellent stereoselectivities (86-96% ee, dr >95:5) and moderate to good yield (50-83%). Their synthetic utility has been well demonstrated by the facile construction of bicyclic lactones bearing 4-5 stereogenic centers.
Related Papers
- → Maleimide as an efficient nucleophilic partner in the aza-Morita–Baylis–Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles(2015)31 cited
- → A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction(2010)5 cited
- → The Morita–Baylis–Hillman Reaction(2019)4 cited
- → ChemInform Abstract: Enantioselective, Organocatalytic Morita—Baylis—Hillman and Aza‐Morita—Baylis—Hillman Reactions: Stereochemical Issues(2011)
- → ChemInform Abstract: Privileged Chiral Catalysts in Asymmetric Morita—Baylis—Hillman/Aza‐Morita—Baylis—Hillman Reaction(2010)