New polymer-supported phosphonate reagents for the synthesis of Z-α,β-unsaturated esters

被引:12
作者
Ando, Kaori [1 ]
Suzuki, Yusaku [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan
关键词
WADSWORTH-EMMONS REACTION; Z-UNSATURATED ESTERS; SOLID-PHASE SYNTHESIS; ETHYL (DIARYLPHOSPHONO)ACETATES; SELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; PURIFICATION; OLEFINATION; ALDEHYDES; AMIDES;
D O I
10.1016/j.tetlet.2010.02.113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New polymer-supported phosphonate reagents have been prepared and evaluated for the synthesis of Z-alpha,beta-unsaturated esters. High Z-selectivity was obtained using the reagent having two o-t-BuC(6)H(4) groups. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2323 / 2325
页数:3
相关论文
共 22 条
[1]   Convenient preparations of (diphenylphosphono)acetic and esters and the comparison of the Z-selectivities of their Horner-Wadsworth-Emmons reaction with aldehydes depending on the ester moiety [J].
Ando, K .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8406-8408
[2]   Z-selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU [J].
Ando, K ;
Oishi, T ;
Hirama, M ;
Ohno, H ;
Ibuka, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4745-4749
[3]   A mechanistic study of the Horner-Wadsworth-Emmons reaction: Computational investigation on the reaction pass and the stereochemistry in the reaction of lithium enolate derived from trimethyl phosphonoacetate with acetaldehyde [J].
Ando, K .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6815-6821
[4]  
Ando K, 2001, SYNLETT, P1272
[5]   Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes [J].
Ando, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8411-8416
[6]   Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates [J].
Ando, K .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1934-1939
[7]   PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE [J].
ANDO, K .
TETRAHEDRON LETTERS, 1995, 36 (23) :4105-4108
[8]   Z-selective Horner-Tadsworth-Emmons reaction [J].
Ando, K .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2000, 58 (09) :869-876
[9]   Bis(2-t-butylphenyl)phosphonoacetamides for the highly cis-selective synthesis of α,β-unsaturated amides [J].
Ando, Kaori ;
Nagaya, Shigeo ;
Tarumi, Yuko .
TETRAHEDRON LETTERS, 2009, 50 (40) :5689-5691
[10]   Horner-Emmons synthesis with minimal purification using ROMPGEL: A novel high-loading matrix for supported reagents [J].
Barrett, AGM ;
Cramp, SM ;
Roberts, RS ;
Zecri, FJ .
ORGANIC LETTERS, 1999, 1 (04) :579-582