Enantioselective Palladium(II)-Catalyzed Formal [3,3]-Sigmatropic Rearrangement of 2-Allyloxypyridines and Related Heterocycles

被引：68

作者：

Rodrigues, Alessandro ^{[1
]}

Lee, Ernest E. ^{[1
]}

Batey, Robert A. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ANGIOTENSIN-CONVERTING ENZYME; AZA-CLAISEN REARRANGEMENT; CATALYTIC ASYMMETRIC REARRANGEMENT; ANODIC AMIDE OXIDATIONS; ALLYLIC AMINES; SIGMATROPIC REARRANGEMENT; STREPTOMYCES-CHROMOFUSCUS; STEREOSELECTIVE-SYNTHESIS; INHIBITOR (-)-A58365A; ALPHA-AMINO;

D O I：

10.1021/ol9025759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of (E)- and (Z)-allyloxy substituted N-heterocycles generates N-allyl N-heterocyclic amides in good yields and high enantioselectivities (up to 96% ee). The chiral palladacycle COP-Cl (5 mol %) is used as a catalyst with silver(I) trifluoroacetate (10 mol %) at 35-45 degrees C. Examples of heterocycles synthesized include 2-pyridones, quinolin-2(1H)-ones, and isoquinolin-1(2H)-ones.

引用

页码：260 / 263

页数：4

共 42 条

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