Amphoteric α-Boryl Aldehydes

被引：137

作者：

He, Zhi ^{[1
]}

Yudin, Andrei K. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 35期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BORON-WITTIG REACTION; POTASSIUM T-BUTOXIDE; STEREOSELECTIVE-SYNTHESIS; ORGANIC-SYNTHESIS; CARBONYL-COMPOUNDS; METHYL; 2-ACETAMIDOACRYLATE; TETRASUBSTITUTED OXIRANES; PETERSON OLEFINATION; DIMESITYLBORON GROUP; ALDOL REACTION;

D O I：

10.1021/ja205910d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new class of stable molecules, alpha-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from alpha-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of alpha-boryl aldehydes in chemical synthesis.

引用

页码：13770 / 13773

页数：4

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