Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)-H allylic alkylation of α,β-unsaturated carbonyls

被引：14

作者：

Mitra, Sankash ^{[1
]}

Sarkar, Rahul ^{[1
]}

Chakrabarty, Aditya ^{[1
]}

Mukherjee, Santanu ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 42期

关键词：

BAYLIS-HILLMAN REACTION; KOJIC ACID; TUMOR PROMOTERS; METAL-COMPLEXES; SUBSTITUTION; DERIVATIVES; ALLYLATION; AMINE; REARRANGEMENT; CYCLOADDITION;

D O I：

10.1039/d2sc03966d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydroxy-directed iridium-catalyzed enantioselective formal beta-C(sp(2))-H allylic alkylation of kojic acid and structurally related alpha,beta-unsaturated carbonyl compounds is developed. This reaction, catalyzed by an Ir(i)/(P,olefin) complex, utilizes the nucleophilic character of alpha-hydroxy alpha,beta-unsaturated carbonyls, to introduce an allyl group at its beta-position in a branched-selective manner in good to excellent yield with uniformly high enantioselectivity (up to >99.9 : 0.1 er). To the best of our knowledge, this report represents the first example of the use of kojic acid in a transition metal catalyzed highly enantioselective transformation.

引用

页码：12491 / 12497

页数：7

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