Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu-H-Catalyzed Si-O Coupling

被引：52
|
作者：
Seliger, Jan [1 ]
Dong, Xichang [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 07期
关键词：
asymmetric catalysis; copper; dehydrogenative coupling; silicon; tertiary alcohols; ASYMMETRIC-SYNTHESIS; ALKYNYL KETONES; SILYLATION; SECONDARY; EFFICIENCY; SCOPE;
D O I：
10.1002/anie.201813229
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst-controlled enantioselective silylation. This non-enzymatic kinetic resolution is catalyzed by a Cu-H species and makes use of the commercially available precatalyst MesCu/(R,R)-Ph-BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl- as well as dialkyl-substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post-functionalization in this position (s up to 207).
引用
收藏
页码：1970 / 1974
页数：5
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