Catalytic Enantioselective Alkynylation of Trifluoromethyl Ketones: Pronounced Metal Fluoride Effects and Implications of Zinc-to-Titanium Transmetallation

被引：73

作者：

Zhang, Guang-Wu ^{[1
]}

Meng, Wei ^{[1
]}

Ma, Hai ^{[1
]}

Nie, Jing ^{[1
]}

Zhang, Wen-Qin ^{[1
]}

Ma, Jun-An ^{[1
,2
]}

机构：

[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期

关键词：

alkynylation; asymmetric catalysis; enantioselectivity; fluorides; titanium; ASYMMETRIC ALKYNYLATION; LITHIUM ACETYLIDE; TERTIARY ALCOHOLS; ALKYNE ADDITIONS; PROCHIRAL KETONE; COMPLEXES; ALDEHYDES; FLUORINATION; GENERATION; REAGENTS;

D O I：

10.1002/anie.201007341

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lost in transmetalation: The titanium(IV)-catalyzed title reaction, utilizing chiral cinchona alkaloids as ligands (L1 and L2), was developed for the synthesis of both enantiomers of trifluoromethylated propargylic tertiary alcohols in high yield and enantioselectivity. Small amounts of BaF2 were found to be essential for maintaining high levels of reactivity and enantioselectivity. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3538 / 3542

页数：5