Organocatalytic α-hydroxymethylation of cyclopentanone with aqueous formaldehyde: Easy access to chiral δ-lactones

被引：29

作者：

Mase, Nobuyuki ^{[1
]}

Inoue, Azusa ^{[1
]}

Nishio, Masaki ^{[1
]}

Takabe, Kunihiko ^{[1
]}

机构：

[1] Shizuoka Univ, Dept Mol Sci, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 14期

基金：

日本学术振兴会;

关键词：

Organocatalysis; Chiral lactone; Jasmine lactone; Aldol reaction; ASYMMETRIC ALDOL REACTIONS; WATER; ACID; RESOLUTION; CATALYSTS;

D O I：

10.1016/j.bmcl.2009.03.012

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Optically active lactones are important synthons in perfume and aroma manufacturing. Therefore, developments of efficient asymmetric syntheses are desired. Organocatalytic asymmetric alpha-hydroxymethylations of cyclopentanone with aqueous formaldehyde have been developed, to furnish the corresponding alpha-(hydroxymethyl) cyclopentanone with high enantioselectivity. Further chemical transformation of alpha-(hydroxymethyl) cyclopentanone gave the key intermediate for jasmine lactone, which is widely found in fruits and flowers. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3955 / 3958

页数：4

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