Iridium-Catalyzed Enantioselective α-Allylic Alkylation of Amides Using Vinyl Azide as Amide Enolate Surrogate

被引：25

作者：

Chakrabarty, Aditya ^{[1
]}

Mukherjee, Santanu ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 19期

关键词：

ASYMMETRIC-SYNTHESIS; 5H-OXAZOL-4-ONES; SUBSTITUTION; ALLYLATION; ALCOHOLS; ACID; CONSTRUCTION; THIOETHERS;

D O I：

10.1021/acs.orglett.0c03002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among the unstabilized enolates used as nucleophiles in iridium-catalyzed asymmetric allylic alkylation reactions, amide enolates are the least explored. Vinyl azides are now employed as amide enolate surrogates in Ir-catalyzed asymmetric allylic alkylation with branched allylic alcohols as the allylic electrophile. Competing reaction pathways are suppressed through the systematic tuning of the steric and electronic properties of vinyl azide to effect the alpha-allylic alkylation of secondary acetamides with high atom economy, exclusive branched selectivity, and mostly excellent enantioselectivity.

引用

收藏

页码：7752 / 7756

页数：5

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