公开(公告)号：US09873713B2

公开(公告)日：2018-01-23

申请号：US14405092

申请日：2014-10-10

Applicant: Zhejiang University

Inventor： Shengming Ma ,  Xin Huang ,  Chunling Fu

IPC: C07H15/18 ,  C07H15/10 ,  C07C29/46 ,  C07C2/86 ,  C07C303/40 ,  C07C231/12 ,  C07C269/06 ,  C07C67/30 ,  C07H1/00 ,  C07C37/14 ,  C07H15/14 ,  C07C29/32 ,  C07C67/343

CPC classification number: C07H15/18 ,  C07B2200/07 ,  C07C2/867 ,  C07C29/32 ,  C07C29/46 ,  C07C37/14 ,  C07C67/30 ,  C07C67/343 ,  C07C231/12 ,  C07C269/06 ,  C07C303/40 ,  C07C2527/122 ,  C07C2601/14 ,  C07H1/00 ,  C07H15/10 ,  C07H15/14 ,  C07C33/02 ,  C07C33/30 ,  C07C33/14 ,  C07C33/38 ,  C07C69/602 ,  C07C69/608 ,  C07C311/16 ,  C07C233/65 ,  C07C271/12 ,  C07C15/44

Abstract: The present invention relates to a process for efficiently synthesizing highly optically active 1,3-disubstituted allenes, i.e., a one-step process for preparing highly optically active 1,3-disubstituted allenes by using a functionalized terminal alkyne, an aldehyde and a chiral α,α-diphenyl prolinol as reactants under the catalysis of a divalent copper salt. The operation of the process is simple, and the raw materials and reagents are readily available. The process has a broad-spectrum of substrates and a good compatibility for a wide variety of functional groups such as glycosidic units, primary alcohols, secondary alcohols, tertiary alcohols, amides, malonates, etc., and does not require the protection for the functional groups. The obtained axially chiral allene has a moderate to high yield and a good diastereoselectivity or enantioselectivity.