METHOD FOR SYNTHESIZING 1,3-DISUBSTITUTED ALLENE WITH HIGH OPTICAL ACTIVITY

Title:

METHOD FOR SYNTHESIZING 1,3-DISUBSTITUTED ALLENE WITH HIGH OPTICAL ACTIVITY

Document Type and Number:

WIPO Patent Application WO/2016/019630

Kind Code:

A1

Abstract:

Disclosed is a method for synthesizing 1,3-disubstituted allene with high optical activity, namely a method for preparing 1,3-disubstituted allene with high optical activity in one step of functionalizing terminal alkyne, aldehyde and chiral α,α-diphenyl-L-prolinol under catalysis of a bivalent copper salt. The method is simple to operate, adopts easily available raw materials and reagents, and uses a substrate that has wide universality, is compatible with a plurality of functional groups such as multiple types of glycosidic units, primary alcohol, secondary alcohol, tertiary alcohol, amides and dimethyl malonate and does not need further protection; and the obtained axial-chirality allene is moderate to good in yield and excellent in diastereoselectivity or enantioselectivity.

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Inventors:

MA SHENGMING (CN)
HUANG XIN (CN)
FU CHUNLING (CN)

Application Number:

PCT/CN2014/088308

Publication Date:

February 11, 2016

Filing Date:

October 10, 2014

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Assignee:

UNIV ZHEJIANG (CN)

International Classes:

C07B53/00; C07C2/88; C07C13/28; C07C15/44; C07C29/32; C07C33/02; C07C33/14; C07C33/30; C07C33/38; C07C67/343; C07C69/587; C07C69/608; C07C269/06; C07C271/12; C07C303/40; C07C311/16; C07H1/00; C07H15/10; C07H15/14; C07H15/18

Foreign References:

CN102617261A

2012-08-01

Other References:

YE, JUNTAO ET AL.: "Studies on ZnBr2-mediated Synthesis of Axially Chiral Aryl-substituted Allenes from Terminal Alkynes, Aromatic Aldehydes and (S)a, a-diphenylprolinol", TETRAHEDRON, vol. 69, no. 42, 12 July 2013 (2013-07-12), pages 8959 - 8963, XP028708787, DOI: doi:10.1016/j.tet.2013.07.021
KUANG, JINQIANG ET AL.: "Copper (I) Iodide-catalyzed One-Step Preparation of Functionalized Allenes from Terminal Alkynes: Amine Effect", ADV. SVNTH. CATAL., vol. 354, no. 5, 7 March 2012 (2012-03-07), pages 933 - 944

Attorney, Agent or Firm:

MSJ LAW OFFICE (CN)
上海麦其知识产权代理事务所（普通合伙） (CN)

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