title: Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones.
abstract: The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng, Henan, 475004, PR China.
authors.forename: Guanghu
authors.initials: G
authors.lastname: Tong
authors.forename: Bo
authors.initials: B
authors.lastname: Zhu
authors.forename: Richmond
authors.initials: R
authors.lastname: Lee
authors.forename: Wenguo
authors.initials: W
authors.lastname: Yang
authors.forename: Davin
authors.initials: D
authors.lastname: Tan
authors.forename: Caiyun
authors.initials: C
authors.lastname: Yang
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Han
authors.forename: Lin
authors.initials: L
authors.lastname: Yan
authors.forename: Kuo-Wei
authors.initials: KW
authors.lastname: Huang
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D002254:Carbonates; D007659:Ketones