A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines

被引：5
|
作者：
Sheng, Jiajun [1 ]
Chang, Huan [1 ]
Qian, Yu [2 ]
Ma, Mingliang [1 ]
Hu, Wenhao [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Mol Engn, Dept Chem, Shanghai 200062, Peoples R China
[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 22期
基金：
中国国家自然科学基金;
关键词：
Paclitaxel side chain; N-Benzoylbenzyl imines; 1,3-Dipolar cycloaddition; Carbonyl ylides; One-pot reaction; ENANTIOSELECTIVE 3-COMPONENT REACTIONS; CHIRAL BRONSTED ACID-RH-2(OAC)(4); MANNICH-TYPE REACTION; BETA-AMINO ALCOHOLS; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; 1,2-AMINO ALCOHOLS; HIGHLY EFFICIENT; DIAZO-COMPOUNDS; ACYL IMINES;
D O I：
10.1016/j.tetlet.2018.01.054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient cascade approach to alpha-hydroxy-beta-amino acid derivatives is reported, which goes through a 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines and followed by hydrolysis under acidic conditions. This is the first example of using N-benzoylbenzyl imine as dipolarophile for 1,3-dipolar cycloaddition with carbonyl ylide, which provides a direct and convenient access for the one-pot synthesis of paclitaxel side chain and its derivatives. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2141 / 2144
页数：4
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