Barbier-type allylation of chiral alpha-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

被引：22

作者：

Rubsam, F ^{[1
]}

Seck, S ^{[1
]}

Giannis, A ^{[1
]}

机构：

[1] UNIV BONN,INST ORGAN CHEM & BIOCHEM,D-53121 BONN,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(97)00050-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：2823 / 2834

页数：12

共 4 条

[1] Enantioselective Barbier-type allylation of ketones using allyl halide and indium in water
Nakamura, Shuichi
Hara, Yoshichika
Furukawa, Takashi
Hirashita, Tsunehisa
RSC ADVANCES, 2017, 7 (25): : 15582 - 15585
[2] Metal-mediated Barbier-type carbonyl allylation under solvent-free conditions
Yi, XH
Haberman, JX
Li, CJ
SYNTHETIC COMMUNICATIONS, 1998, 28 (16) : 2999 - 3009
[3] Diastereoselective allylation of aldehydes with an enantiopure 2-sulfinylallyl halide under environmentally friendly Barbier-type conditions
Márquez, F
Llebaria, A
Delgado, A
ORGANIC LETTERS, 2000, 2 (04) : 547 - 549
[4] A MILD AND CONVENIENT BARBIER-TYPE ALLYLATION OF ALDEHYDES TO HOMOALLYLIC ALCOHOLS VIA IODIDE-ION PROMOTED STANNYLATION OF ALLYLIC BROMIDES AND CHLORIDES WITH TIN(II) CHLORIDE
IMAI, T
NISHIDA, S
SYNTHESIS-STUTTGART, 1993, (04): : 395 - 399

← 1 →