Novel and practical asymmetric synthesis of β2,3-amino esters using asymmetric Michael addition of chiral amine

被引：3

作者：

Ozeki, Minoru ^{[1
]}

Egawa, Honoka ^{[1
]}

Takano, Toshiki ^{[1
]}

Mizutani, Hideki ^{[1
]}

Yasuda, Narumi ^{[1
]}

Arimitsu, Kenji ^{[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, 1 Shichono Cho, Kyoto 6078412, Japan

[2] Ritsumeikan Univ, Coll Pharmaceut Sci, Med Organ Chem Lab, I-1-1 Noji Higashi, Kusatsu, Shiga 5258577, Japan

来源：

TETRAHEDRON | 2017年 / 73卷 / 15期

关键词：

beta(2,3)-Amino acid; Asymmetric Michael addition; Face-selective protonation; Chiral amine; Trisubstituted; (E)-alpha; beta-unsaturated ester; PARALLEL KINETIC RESOLUTION; STEREOSELECTIVE-SYNTHESIS; CONJUGATE ADDITION; DERIVATIVES; ACIDS; 3-ALKYL-CISPENTACIN; CONSTRUCTION; CENTERS;

D O I：

10.1016/j.tet.2017.02.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for the synthesis of chiral beta(2,3)-amino esters having various substituents was developed, which is characterized by an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted (E)-alpha,beta-unsaturated esters. We found that a highly face-selective protonation occurred by the quick addition of water to the enolate intermediate derived from the Michael addition reaction to afford N-protected beta(2,3)-amino esters in moderate to excellent yields. This finding was made possible by the facile preparation of geometrically pure trisubstituted (E)-alpha,beta-unsaturated esters, which was established recently by our group. The subsequent deprotection of the amino group in the Michael adduct by using N-iodosuccinimide (NIS) efficiently provided beta(2,3)-amino esters having various substituents. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2014 / 2021

页数：8