Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles

被引：63
作者：
Archambeau, Alexis [1 ]
Rovis, Tomislav [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 45期
关键词：
4; pi-electrocyclization; azabicycles; C-H insertion; 1,3-migration; rhodium; C-H ACTIVATION; N BOND FORMATION; INTERMOLECULAR AMIDATION; ACRYLIC-ACIDS; ALKYNES; FUNCTIONALIZATION; BENZAMIDES; PHENOXYACETAMIDES; AMINATION; ARENES;
D O I：
10.1002/anie.201504150
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unsaturated N-sulfonamides undergo a Rh-III- catalyzed allylic C(sp(3))H activation followed by insertion with an exogenous internal alkyne. The reaction generates [3.3.0], [4.3.0], and [5.3.0] azabicyclic structures with excellent diastereoselectivity. Deuterium labeling experiments implicate a 1,3-Rh shift as a key step in the mechanism.
引用
收藏
页码：13337 / 13340
页数：4
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