Practical and Highly Stereoselective Synthesis of Trisubstituted (E)-α,β-Unsaturated Esters

被引：4

作者：

Ozeki, Minoru ^{[1
]}

Egawa, Honoka ^{[1
]}

Kuse, Akiko ^{[1
]}

Takano, Toshiki ^{[1
]}

Yasuda, Narumi ^{[1
]}

Mizutani, Hideki ^{[1
]}

Izumiya, Sumire ^{[1
]}

Nakashima, Daichi ^{[1
]}

Arimitsu, Kenji ^{[1
]}

Miura, Takuya ^{[1
]}

Kajimoto, Tetsuya ^{[1
,2
]}

Hosoi, Shinzo ^{[1
]}

Iwasaki, Hiroki ^{[1
]}

Kojima, Naoto ^{[1
]}

Node, Manabu ^{[1
]}

Yamashita, Masayuki ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Dept Pharmaceut Mfg Chem, Yamashina Ku, Kyoto 6078414, Japan

[2] Ritsumeikan Univ, Res Ctr Drug Discovery & Pharmaceut Dev Sci, Res Org Sci & Technol, Kusatsu, Shiga 5258577, Japan

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 21期

基金：

日本学术振兴会;

关键词：

stereoselective synthesis; enoates; aldol reactions; acylations; elimination reactions; BAYLIS-HILLMAN ADDUCTS; SERINE-PROTEASE INHIBITORS; WADSWORTH-EMMONS REACTION; BETA-AMINO ACIDS; CONJUGATE ADDITION; UNSATURATED ESTERS; INSECT PHEROMONES; SIMPLE ACCESS; EFFICIENT; OLEFINS;

D O I：

10.1055/s-0034-1378786

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trisubstituted (E)-alpha,beta-unsaturated esters bearing various substituents were synthesized with high geometrical selectivity by using three reactions: an aldol reaction, acetylation of the hydroxy group at the beta-position, and an E1cB reaction induced by 1,8-diazabicyclo[5.4.0]undec-7-ene. The method does not require separation of the diastereoisomeric mixture of beta-hydroxy ester intermediates before the E1cB reaction, and is usable for gram-scale syntheses of trisubstituted (E)-alpha,beta-unsaturated esters.

引用

页码：3392 / 3402

页数：11

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