The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jan. 23, 2018

Filed:

Oct. 10, 2014
Applicant:

Zhejiang University, Hangzhou, Zhejiang, CN;

Inventors:

Shengming Ma, Hangzhou, CN;

Xin Huang, Hangzhou, CN;

Chunling Fu, Hangzhou, CN;

Assignee:

ZHEJIANG UNIVERSITY, Hangzhou, Zhejiang, CN;

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07H 15/18 (2006.01); C07H 15/10 (2006.01); C07C 29/46 (2006.01); C07C 2/86 (2006.01); C07C 303/40 (2006.01); C07C 231/12 (2006.01); C07C 269/06 (2006.01); C07C 67/30 (2006.01); C07H 1/00 (2006.01); C07C 37/14 (2006.01); C07H 15/14 (2006.01); C07C 29/32 (2006.01); C07C 67/343 (2006.01);
U.S. Cl.
CPC ...
C07H 15/18 (2013.01); C07C 2/867 (2013.01); C07C 29/32 (2013.01); C07C 29/46 (2013.01); C07C 37/14 (2013.01); C07C 67/30 (2013.01); C07C 67/343 (2013.01); C07C 231/12 (2013.01); C07C 269/06 (2013.01); C07C 303/40 (2013.01); C07H 1/00 (2013.01); C07H 15/10 (2013.01); C07H 15/14 (2013.01); C07B 2200/07 (2013.01); C07C 2527/122 (2013.01); C07C 2601/14 (2017.05);
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.


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