Super silyl group for diastereoselective sequential reactions: Access to complex chiral architecture in one pot

被引：84

作者：

Boxer, Matthew B. ^{[1
]}

Yamamoto, Hisashi ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 10期

关键词：

D O I：

10.1021/ja0693542

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.

引用

页码：2762 / +

页数：3

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