An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

被引：5

作者：

Wu, Zhen ^{[1
,2
]}

Feng, Xue-Xin ^{[1
,2
]}

Wang, Qing-Dong ^{[2
]}

Liu, Xuan-Yu ^{[1
]}

Rao, Weidong ^{[3
]}

Yang, Jin-Ming ^{[1
,2
]}

Shen, Zhi-Liang ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

[2] Yancheng Teachers Univ, Sch Pharm, Yancheng 224007, Peoples R China

[3] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 02期

关键词：

Bismuth; Ammonium iodide; Water; Homoallylic alcohol; Diastereoselectivity; UNACTIVATED ALKYL-HALIDES; GRIGNARD-TYPE ADDITION; C-H BONDS; CARBONYL-COMPOUNDS; ORGANIC-REACTIONS; ALPHA; BETA-UNSATURATED KETONES; QUATERNARY CENTERS; IN-SITU; ORGANOINDIUM REAGENTS; ASYMMETRIC-SYNTHESIS;

D O I：

10.1016/j.cclet.2019.07.030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate. 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：391 / 395

页数：5

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