Asymmetric rearrangement of racemic epoxides catalyzed by chiral Brønsted acids.
This paper describes a chiral Brønsted acid catalyzed asymmetric 1,2-rearrangement of racemic epoxides via a hydrogen-shift process for the synthesis of chiral aldehydes, and, followed by a reduction, a variety of optically active alcohols can be furnished in moderate yields with up to 50% ee. Especially, a facile one-pot synthesis of chiral alcohols directly from simple alkenes by a sequential epoxidation, rearrangement, and reduction has also been realized.
Beijing National Laboratory of Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Minyang
M
Zhuang
Haifeng
H
Du
D000143:Acids / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000143:Acids; D000438:Alcohols; D000447:Aldehydes; D004852:Epoxy Compounds