Lithium Binaphtholate-Catalyzed Enantioselective Enyne Addition to Ketones: Access to Enynylated Tertiary Alcohols

被引：18

作者：

Cai, Hua

Nie, Jing

Zheng, Yan

Ma, Jun-An ^{[1
]}

机构：

[1] Tianjin Univ, Minist Educ, Dept Chem, Key Lab Syst Bioengn, Tianjin 300072, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 12期

基金：

中国国家自然科学基金;

关键词：

CHIRAL BRONSTED ACID; MANNICH-TYPE REACTION; BASE AMINO-ALCOHOLS; ASYMMETRIC ALKYNYLATION; AROMATIC KETONES; TRIFLUOROMETHYL KETONES; ALDEHYDES; COMPLEX; PHENYLACETYLENE; 1,3-DIYNES;

D O I：

10.1021/jo5005839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new catalytic enantioselective enyne addition to ketones has been developed. In the presence of chiral lithium binaphtholate, the addition reaction proceeded smoothly to produce a series of enynylated tertiary alcohols in up to 96% yield and 94% enantiomeric excess. Convenient transformation of the adduct via Pauson-Khand cycloaddition reaction afforded the bicyclic product without detectable loss of enantioselectivity. Furthermore, catalytic asymmetric enyne addition to trifluoromethylketone was applied in the synthesis of the Efavirenz analogue.

引用

收藏

页码：5484 / 5493

页数：10

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