One-carbon homologation of carboxylic acids via BtCH2TMS:: A safe alternative to the Arndt-Eistert reaction

被引:22
作者
Katritzky, AR [1 ]
Zhang, SM
Hussein, AHM
Fang, YF
Steel, PJ
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
[2] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand
关键词
D O I
10.1021/jo0017640
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboxylic acids are converted into the corresponding homologated acids or esters, using easily available 1-(trimethylsilylmethyl)benzotriazole (1) as a one-carbon synthon. The effectiveness of the reaction has been investigated on six aryl and seven alkyl carboxylic acids.
引用
收藏
页码:5606 / 5612
页数:7
相关论文
共 35 条
[1]  
Aller E, 2000, SYNLETT, P526
[2]   Resolution of a citric acid derivative: synthesis of (R)-(-)-homocitric acid-gamma-lactone [J].
Ancliff, RA ;
Russell, AT ;
Sanderson, AJ .
TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3379-3382
[3]   Two carbon homologation of carboxylic acids using acrylamide as a radical trap [J].
Barton, DHR ;
Liu, WS .
TETRAHEDRON LETTERS, 1997, 38 (14) :2431-2434
[4]  
BARTON DHR, 1991, TETRAHEDRON LETT, V32, P3309
[5]   HOMOLOGATION OF CARBOXYLIC-ACIDS BY IMPROVED METHODS BASED ON RADICAL CHAIN CHEMISTRY OF ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE [J].
BARTON, DHR ;
CHERN, CY ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (35) :5013-5016
[6]   Two-carbon homologation of aldehydes via silyl ketene acetals:: A new stereoselective approach to (E)-alkenoic acids [J].
Bellassoued, M ;
Lensen, N ;
Bakasse, M ;
Mouelhi, S .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8785-8789
[7]   A NEW AND EASY ROUTE TO (2E,4E)-DIENALS BY 4-CARBON HOMOLOGATION OF ALDEHYDES [J].
BELLASSOUED, M ;
SALEMKOUR, M .
TETRAHEDRON LETTERS, 1993, 34 (33) :5281-5284
[8]  
CABEZAS JA, 1995, TETRAHEDRON LETT, V36, P5127
[9]   Preparation of N-Fmoc-protected β2- and β3-amino acids and their use as building blocks for the solid-phase synthesis of β-peptides [J].
Guichard, G ;
Abele, S ;
Seebach, D .
HELVETICA CHIMICA ACTA, 1998, 81 (02) :187-206
[10]   REACTIONS OF CARBON MONOXIDE WITH THIOLS, SULFIDES, AND DISULFIDES [J].
HOLMQUIST, HE ;
CARNAHAN, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (12) :2240-2242