Z-Selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes

被引:11
作者
Ando, Kaori [1 ]
Sato, Kaori [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan
关键词
Z-UNSATURATED ESTERS; ETHYL (DIARYLPHOSPHONO)ACETATES; ANISOMELIC ACID; OLEFINATION; ALDEHYDES; STEREOCHEMISTRY; CYCLIZATION; EFFICIENT; REAGENTS; BASE;
D O I
10.1016/j.tetlet.2011.01.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1284 / 1287
页数:4
相关论文
共 29 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]   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
[5]   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
[6]   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
[7]   Z-selective Horner-Tadsworth-Emmons reaction [J].
Ando, K .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2000, 58 (09) :869-876
[8]   New polymer-supported phosphonate reagents for the synthesis of Z-α,β-unsaturated esters [J].
Ando, Kaori ;
Suzuki, Yusaku .
TETRAHEDRON LETTERS, 2010, 51 (17) :2323-2325
[9]   Z-Selective Intramolecular Horner-Wadsworth-Emmons Reaction for the Synthesis of Macrocyclic Lactones [J].
Ando, Kaori ;
Narumiya, Kenji ;
Takada, Hirokazu ;
Teruya, Taiji .
ORGANIC LETTERS, 2010, 12 (07) :1460-1463
[10]   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