Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols

被引：17

作者：

Xu, Weiliang ^{[2
]}

Zhou, Yonggui ^{[1
]}

Wang, Ruimin ^{[3
]}

Wu, Guotao ^{[1
]}

Chen, Ping ^{[1
]}

机构：

[1] Dalian Inst Chem Phys, Dalian, Peoples R China

[2] Natl Univ Singapore, Singapore 117548, Singapore

[3] Inner Mongolia Univ, Hohhot, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 02期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; AMMONIA-BORANE; SODIUM-BOROHYDRIDE; CARBONYL-COMPOUNDS; MECHANISTIC ASPECTS; METAL AMIDOBORANES; CONJUGATED KETONES; STORAGE MATERIAL; ALDEHYDES; RELEASE;

D O I：

10.1039/c1ob06368e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing alpha,beta-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.

引用

页码：367 / 371

页数：5

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