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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.

Inventors:
MA, Shengming (Department of Chemistry, Zhejiang UniversityNo. 38 Zheda Road, West Lake Distric, Hangzhou Zhejiang 7, 310027, CN)
HUANG, Xin (Department of Chemistry, Zhejiang UniversityNo. 38 Zheda Road, West Lake Distric, Hangzhou Zhejiang 7, 310027, CN)
FU, Chunling (Department of Chemistry, Zhejiang UniversityNo. 38 Zheda Road, West Lake Distric, Hangzhou Zhejiang 7, 310027, CN)
Application Number:
CN2014/088308
Publication Date:
February 11, 2016
Filing Date:
October 10, 2014
Export Citation:
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Assignee:
ZHEJIANG UNIVERSITY (No. 38 Zheda Road, West Lake DistrictHangzhou, Zhejiang 7, 310027, 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:
CN102617261A2012-08-01
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 (Maggie Dong, Room 301B Building 3, No. 155, Jinshajiang Road, Putuo District, Shanghai 2, 200062, CN)
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