Stereoselective 1,4-Addition of Primary Alcohols to γ-Alkoxy-α,β-unsaturated Esters

被引：0

作者：

Inatomi, Saki ^{[1
]}

Takayanagi, Yuta ^{[1
]}

Watanabe, Kento ^{[1
]}

Toita, Akinori ^{[1
]}

Yamakoshi, Hiroyuki ^{[1
]}

Nakamura, Seiichi ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, 3-1 Tanabe Dori, Nagoya, Aichi 4678603, Japan

来源：

SYNTHESIS-STUTTGART | 2021年 / 53卷 / 01期

关键词：

1,4-addition; gamma-alkoxy-alpha; beta-unsaturated esters; primary alcohols; syn-selectivity; cyclic acetals; ASYMMETRIC CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; TETRAHYDROPYRAN; HYDRATION; ACIDS;

D O I：

10.1055/s-0040-1707274

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope and limitations of the diastereoselective 1,4-addition reaction of primary alcohols to gamma-alkoxy-alpha,beta-unsaturated esters were investigated. We found that a variety of sodium alkoxides, generated from the corresponding primary alcohols with NaH, underwent 1,4-addition reactions with (E)-enoates in CH(2)Cl(2)at -23 degrees C to give beta-alkoxy esters in modest yields with good to excellentsyn-selectivity, whereas stereoselectivity was not observed with the use of glycerol derivatives as nucleophiles. Cyclic acetal protection was found to play a pivotal role for the reaction to proceed.

引用

页码：161 / 174

页数：14

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