Invention Grant
- Patent Title: Process for synthesizing highly optically active 1,3-disubstituted allenes
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Application No.: US14405092Application Date: 2014-10-10
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Publication No.: US09873713B2Publication Date: 2018-01-23
- Inventor: Shengming Ma , Xin Huang , Chunling Fu
- Applicant: Zhejiang University
- Applicant Address: CN Hangzhou, Zhejiang
- Assignee: ZHEJIANG UNIVERSITY
- Current Assignee: ZHEJIANG UNIVERSITY
- Current Assignee Address: CN Hangzhou, Zhejiang
- Agency: Birch, Stewart, Kolasch & Birch, LLP
- Priority: CN201410384975 20140806
- International Application: PCT/CN2014/088308 WO 20141010
- International Announcement: WO2016/019630 WO 20160211
- Main IPC: C07H15/18
- 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

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.
Public/Granted literature
- US20160185812A1 PROCESS FOR SYNTHESIZING HIGHLY OPTICALLY ACTIVE 1,3-DISUBSTITUTED ALLENES Public/Granted day:2016-06-30
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