Highly efficient Mukaiyama-Mannich addition of α-diazo silyl enolate with nitrones catalyzed by MgI2 etherate

被引：2
|
作者：
Meng, Xiangwei [1 ]
Pan, Haokun [1 ]
Zhu, Gaoyang [1 ]
Zhang, Xingxian [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
来源：
TETRAHEDRON | 2020年 / 76卷 / 22期
基金：
中国国家自然科学基金;
关键词：
Nitrone; Diazo silyl enolate; MgI2; etherate; Diazo hydroxylamine; Chemoselectivity; DIELS-ALDER ADDITION; 1,3-DIPOLAR CYCLOADDITIONS; ORGANIC-SYNTHESIS; BUILDING-BLOCKS; ALDOL REACTION; COPPER; CARBENE; ALDEHYDES; INSERTION; REARRANGEMENT;
D O I：
10.1016/j.tet.2020.131167
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Functionalized diazo hydroxylamines are prepared by an efficient Mukaiyama-Mannich addition of alpha-diazo silyl enolate with nitrones under mild reaction conditions. This protocol provides a variety of 1,2-addition adducts in good to excellent yields, which are potentially of great importance in medicinal chemistry. MgI2 etherate (MgI2 center dot(OEt2)(n)) is the preferred catalyst and this addition proceeds without decomposition of the diazo moiety. Furthermore, this MgI2 center dot(OEt2)(n) catalyzed reaction shows unique chemoselectivity towards nitrones with aldehydes or aldimines. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：8
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