Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone

被引：35

作者：

Gao, YuZhe ^{[1
]}

Wang, Xue ^{[1
]}

Sun, LiDong ^{[1
]}

Xie, LongGuan ^{[1
]}

Xu, XiaoHua ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 20期

基金：

中国国家自然科学基金;

关键词：

CARBONYL-COMPOUNDS; ORGANOMETALLIC REACTIONS; CATALYZED ALLYLATION; ORGANIC-SYNTHESIS; METAL; TIN; INTERMEDIATE; ALCOHOLS; BISMUTH; HALIDES;

D O I：

10.1039/c2ob25397f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous solvents was developed to provide an efficient route to alpha-methylene-gamma-butyrolactone, which is synthetically very useful. The desired products were obtained in moderate to high yields in aqueous solvents. Excellent drs were achieved, among which the best diastereomeric ratios of products were found when water was used in the indium-mediated reaction, and THF-NH4Cl (sat, aq) (2 : 1) mixture in the zinc-mediated reaction. Furthermore, the allylation can be induced by chiral centers, especially those in the alpha-position, as a substrate-controlled reaction to obtain the enantioselective homoallylation alcohols.

引用

页码：3991 / 3998

页数：8

共 5 条

[1] Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols
Hirayama, LC
Gamsey, S
Knueppel, D
Steiner, D
DeLaTorre, K
Singaram, B
TETRAHEDRON LETTERS, 2005, 46 (13) : 2315 - 2318
[2] Diastereoselection during 1,2-addition of 3-bromomethyl-5H-furan-2-one to α-chiral aldehydes mediated by indium in aqueous and organic solvent systems: direct route to obtain optically active α-methylene-γ-butyrolactones
Zhang, Fuhai
Liu, Yang
Xie, Longguan
Xu, Xiaohua
RSC ADVANCES, 2014, 4 (33): : 17218 - 17221
[3] Zinc-Mediated Asymmetric Allylation of Chiral N-tert-Butanesulfinyl Aldimines with 3-Bromomethyl-5H-furan-2-one
Shen, An
He, Zhi-Tao
Yu, Hong-Jie
Fukui, Yuki
Tian, Ping
Lin, Guo-Qiang
SYNLETT, 2013, 24 (13) : 1649 - 1656
[4] Pd-catalyzed diastereoselective allylation of aldehydes with 3-bromomethyl-5H-furan-2-one: stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylenec-γ-butyrolactones with a syn configuration
Zhang, Fuhai
Yang, Yanxin
Xie, Longguan
Xu, Xiaohua
CHEMICAL COMMUNICATIONS, 2013, 49 (41) : 4697 - 4699
[5] Indium and zinc-mediated Barbier-type addition reaction of 2,3-allenals with allyl bromide: an efficient synthesis of 1,5,6-alkatrien-4-ols
Kong, Wangqing
Fu, Chunling
Ma, Shengming
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (24) : 4587 - 4592

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