Catalytic enantioselective addition of terminal 1,3-diynes to aromatic ketones: facile access to chiral nonracemic tertiary alcohols

Tian-Lin Liu; Hai Ma; Fa-Guang Zhang; Yan Zheng; Jing Nie; Jun-An Ma

doi:10.1039/c1cc15968b

Catalytic enantioselective addition of terminal 1,3-diynes to aromatic ketones: facile access to chiral nonracemic tertiary alcohols

Chem Commun (Camb). 2011 Dec 28;47(48):12873-5. doi: 10.1039/c1cc15968b. Epub 2011 Nov 9.

Authors

Tian-Lin Liu¹, Hai Ma, Fa-Guang Zhang, Yan Zheng, Jing Nie, Jun-An Ma

Affiliation

¹ Department of Chemistry, Tianjin University, Tianjin 300072, China.

PMID: 22068909
DOI: 10.1039/c1cc15968b

Abstract

An efficient, catalytic, and enantioselective 1,2-addition of terminal 1,3-diynes to aromatic ketones was realized in the presence of 10 mol% of a Cu(OTf)(2)-hydroxycamphor-sulfonamide complex, affording chiral tertiary alcohols in up to 94% yield and 90% ee.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Catalysis
Coordination Complexes / chemical synthesis
Coordination Complexes / chemistry
Copper / chemistry
Crystallography, X-Ray
Diynes / chemistry*
Ketones / chemistry*
Molecular Conformation
Stereoisomerism

Substances

Alcohols
Coordination Complexes
Diynes
Ketones
Copper