Efficient asymmetric synthesis of 2,3-diamino-3-phenylpropanoic acid derivatives

被引：49

作者：

Lee, SH

Yoon, J ^{[1
]}

Chung, SH

Lee, YS

机构：

[1] Silla Univ, Dept New Mat Chem, Pusan 617736, South Korea

[2] Seoul Natl Univ, Sch Chem Engn, Seoul 151742, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 11期

基金：

新加坡国家研究基金会;

关键词：

2,3-diamino-3-phenylpropanoic acid derivatives; isopropyl cinnamate; catalytic hydrogenation;

D O I：

10.1016/S0040-4020(01)00090-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, stereoselective synthesis of selectively-protected anti and syn, methyl 2-amino-3-Boc-amino)-3-phenylpropanoate is described. Preparation of syn beta -acetylamino-alpha -hydroxy ester was from isopropyl cinnamate via an acetamide-based Sharpless aminohydroxylation (AA), and its anti isomer was obtained via C-alpha epimerization of the syn isomer. For the installation of a second amino group, two different approaches, involving substitution of the beta -hydroxyl group with azide, were investigated. The first was a ring-opening reaction of trans-oxazoline-5-carboxylate with trimethylsilyl azide, which produced anti beta-(acetylamino)-alpha -azido esters, which then transformed into the anti isomer; whereas the cis-oxazoline-5-carboxylate was found to be unreactive under this reaction condition. The second approach used the Mitsunobu reaction of syn and anti beta-(Boc-amino)-alpha -hydroxy esters with hydrazoic acid, followed by catalytic hydrogenation, which gave both anti and syn isomers, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2139 / 2145

页数：7

共 30 条

[11] Efficient syntheses and ring-opening reactions of trans- and cis-oxazoline-5-carboxylates
Lee, SH
Yoon, J
Nakamura, K
Lee, YS
[J]. ORGANIC LETTERS, 2000, 2 (09) : 1243 - 1246
[12] REACTIONS WITH ORGANOPHOSPHORUS COMPOUNDS .41. NEW PREPARATIVE METHODS USING TRIPHENYLPHOSPHINE-DIETHYL-AZODICARBOXYLATE-HYDROXYCOMPOUND
LOIBNER, H
ZBIRAL, E
[J]. HELVETICA CHIMICA ACTA, 1976, 59 (06) : 2100 - 2113
[13] Stereoselective synthesis of β-substituted α,β-diamino acids from β-hydroxy amino acids
Luo, Y
Blaskovich, MA
Lajoie, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 6106 - 6111
[14] Totally stereocontrolled synthesis of α,β-diamino acids by addition of Grignard reagents to nitrones derived from L-serine
Merino, P
Lanaspa, A
Merchan, FL
Tejero, T
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 629 - 646
[15] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS
MITSUNOBU, O
[J]. SYNTHESIS-STUTTGART, 1981, (01): : 1 - 28
[16] Preparation of aminated taxol side chain precursors. A simple approach to 2,3-diamino acids using the beta-lactam synthon method.
Moyna, G
Williams, HJ
Scott, AI
[J]. SYNTHETIC COMMUNICATIONS, 1997, 27 (09) : 1561 - 1567
[17] O'Brien P, 1999, ANGEW CHEM INT EDIT, V38, P326, DOI 10.1002/(SICI)1521-3773(19990201)38:3<326::AID-ANIE326>3.0.CO
[18] 2-T
[19] Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the beta-lactam synthon method
Ojima, I
Delaloge, F
[J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) : 377 - 386
[20] RECENT ADVANCES IN THE BETA-LACTAM SYNTHON METHOD
OJIMA, I
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) : 383 - 389

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