Nucleophilic Addition of Amines to Ruthenium Carbenes: ortho-(Alkynyloxy)benzylamine Cyclizations towards 1,3-Benzoxazines

被引：54
作者：
Gonzalez-Rodriguez, Carlos [1 ,2 ]
Ramon Suarez, Jose [1 ,2 ]
Varela, Jesus A. [1 ,2 ]
Saa, Carlos [1 ,2 ]
机构：
[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain
[2] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 09期
关键词：
benzoxazines; carbenes; cyclization; rearrangements; ruthenium; FUNCTIONAL CONJUGATED DIENES; C-H FUNCTIONALIZATION; AMMONIUM YLIDES; DIAZO-COMPOUNDS; ASYMMETRIC-SYNTHESIS; CATALYZED REACTIONS; EFFICIENT SYNTHESIS; METAL CARBENOIDS; BETA-KETOESTERS; PART;
D O I：
10.1002/anie.201410284
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new ruthenium-catalyzed cyclization of ortho-(alkynyloxy)benzylamines to dihydro-1,3-benzoxazines is reported. The cyclization is thought to take place via the vinyl ruthenium carbene intermediates which are easily formed from [Cp*RuCl(cod)] and N2CHSiMe3. The mild reaction conditions and the efficiency of the procedure allow the easy preparation of a broad range of new 2-vinyl-2-substituted 1,3-benzoxazine derivatives. Rearrangement of an internal C(sp) in the starting material into a tetrasubstituted C(sp(3)) atom in the final 1,3-benzoxazine is highly remarkable.
引用
收藏
页码：2724 / 2728
页数：5
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