title: Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.
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.
authors.affiliation: Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, China.
authors.forename: Hai-Lei
authors.initials: HL
authors.lastname: Cui
authors.forename: Ji-Rong
authors.initials: JR
authors.lastname: Huang
authors.forename: Jie
authors.initials: J
authors.lastname: Lei
authors.forename: Zhao-Feng
authors.initials: ZF
authors.lastname: Wang
authors.forename: Shi
authors.initials: S
authors.lastname: Chen
authors.forename: Li
authors.initials: L
authors.lastname: Wu
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D002254:Carbonates; D002930:Cinchona Alkaloids; C004511:butenolide; D015107:4-Butyrolactone