Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes

被引：34
|
作者：
Onyeagusi, Chibueze, I [1 ]
Shao, Xinxin [1 ]
Malcolmson, Steven [1 ]
机构：
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 04期
关键词：
ENANTIOSELECTIVE ADDITION; ASYMMETRIC-SYNTHESIS; UMPOLUNG ADDITION; BRONSTED ACID; PALLADIUM; CONSTRUCTION; REAGENTS; PRONUCLEOPHILES; ALCOHOLS; IMINES;
D O I：
10.1021/acs.orglett.0c00342
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic alpha-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo gamma-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.
引用
收藏
页码：1681 / 1685
页数：5
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