Asymmetric synthesis of all four stereoisomers of 1-amino-3-hydroxy-cyclopentane-1-carboxylic acid

被引：2

作者：

Jakubowska, Anna ^{[1
]}

Pabel, Joerg ^{[2
]}

Zylewski, Marek ^{[3
,4
]}

Wanner, Klaus T. ^{[2
]}

Kulig, Katarzyna ^{[1
,2
]}

机构：

[1] Jagiellonian Univ, Coll Med, Chair Pharmaceut Chem, Dept Physicochem Drug Anal,Fac Pharm, PL-30688 Krakow, Poland

[2] Univ Munich, Ctr Drug Res, Dept Pharm, D-81377 Munich, Germany

[3] Jagiellonian Univ, Coll Med, Fac Pharm, Chair Organ Chem,NMR Lab, PL-30688 Krakow, Poland

[4] Jagiellonian Ctr Innovat, NMR Lab, PL-30348 Krakow, Poland

来源：

TETRAHEDRON | 2015年 / 71卷 / 04期

关键词：

Amino acids; Asymmetric synthesis; Glycine equivalent; ALPHA-AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; CYCLIC SULFITES; GLYCINE EQUIVALENT; RECENT PROGRESS; DERIVATIVES; DISCOVERY; PEPTIDES; SULFATES; POTENT;

D O I：

10.1016/j.tet.2014.12.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of all four stereoisomers of 1-amino-3-hydroxy-cyclopentane-1-carboxylic acid based on a chiral glycine equivalent, oxazinone derivative is presented. The crucial point of the performed reactions is the allcylation of (S)- and (R)-glycine equivalent with the respective stereoisomers of 4-(2-iodoethyl)-1,3,2-dioxathiolan-2-oxide using phosphazenic base t-BuP4. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：686 / 693

页数：8

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