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

共 50 条

[31] Design of chiral organocatalysts for practical asymmetric synthesis of amino acid derivatives
Maruoka, Keiji
Ooi, Takashi
Kano, Taichi
CHEMICAL COMMUNICATIONS, 2007, (15) : 1487 - 1495
[32] A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1 2,3-oxathiazolidine-2-oxide:: Practical asymmetric synthesis of (R)-sibutramine
Han, ZX
Krishnamurthy, D
Senanayake, CH
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (02) : 327 - 333
[33] A multicomponent approach to the synthesis of N-sulfonyl β2,3-amino esters
Le Gall, Erwan
Sengmany, Stephane
Samb, Issa
Benakrour, Sabrina
Colin, Christopher
Pignon, Antoine
Leonel, Eric
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (21) : 3423 - 3426
[34] Asymmetric Reformatsky-Type Reaction of Isatin-Derived N-Sulfinyl Ketimines: Efficient and Practical Synthesis of Enantiopure Chiral 2-Oxoindolinyl-3,3-Amino Esters
Su, Lin
Xu, Ming-Hua
SYNTHESIS-STUTTGART, 2016, 48 (16): : 2595 - 2602
[35] Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition α-alkylation
Enders, D
Müller, SF
Raabe, G
SYNLETT, 1999, (06) : 741 - 743
[36] Asymmetric synthesis of β-amino-cyclohexyl sulfonates via aza Michael addition
Enders, D
Wallert, S
SYNLETT, 2002, (02) : 304 - 306
[37] Practical copper-catalyzed asymmetric synthesis of chiral chrysanthemic acid esters
Itagaki, Makoto
Suenobu, Katsuhiro
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 509 - 518
[38] ASYMMETRIC NUCLEOPHILIC ACYLATION VIA METALATED CHIRAL AMINO CYANIDES - ENANTIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED 4-OXOESTERS BY ASYMMETRIC MICHAEL ADDITION
ENDERS, D
GERDES, P
KIPPHARDT, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1990, 29 (02) : 179 - 181
[39] Efficient asymmetric addition of diethylzinc to aldehydes using C2-novel chiral pyridine -amino alcohols as chiral ligands
Zhang, Weijie
Tang, Ruiren
Yu, Huirong
Gao, Shu
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (07) : 545 - 551
[40] Asymmetric Michael addition of α-fluoro-α-nitro esters to nitroolefins: towards synthesis of α-fluoro-α-substituted amino acids
Kwiatkowski, Jacek
Lu, Yixin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (08) : 2350 - 2359

← 1 2 3 4 5 →