A practical stereoselective synthesis of both enantiomers of threo- and erythro-β-hydroxy norvaline from (S)-serine derivatives

被引：18

作者：

Andrés, JM ^{[1
]}

de Elena, N ^{[1
]}

Pedrosa, R ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON | 2000年 / 56卷 / 11期

关键词：

diastereoselective synthesis; aminoalcohols; alkylzincs; aminoaldehydes;

D O I：

10.1016/S0040-4020(00)00038-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four enantiopure diastereoisomers of beta-hydroxy norvaline have been prepared from L-serine in moderate chemical yield. The method is based on the diastereoselective addition of different organometallics to easily accessible serinal derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1523 / 1531

页数：9

共 45 条

[1] KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM [J].

ABIKO, A ;

ROBERTS, JC ;

TAKEMASA, T ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1986, 27 (38) :4537-4540

[2] Stereodivergent synthesis of all diastereomers of 4-aminoheptane-3,5-diol from (L)-serine [J].

Andrés, JM ;

Pedrosa, R .

TETRAHEDRON, 1998, 54 (21) :5607-5616

[3] A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal [J].

Andres, JM ;

Pedrosa, R .

TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2493-2498

[4] Synthesis of enantiopure syn-beta-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to alpha-(dibenzylamino) aldehydes [J].

Andres, JM ;

Barrio, R ;

Martinez, MA ;

Pedrosa, R ;

PerezEncabo, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4210-4213

[5]

BLANK S, 1993, LIEBIGS ANN CHEM, P889

[6]

BLASER D, 1991, LIEBIGS ANN CHEM, P1067

[7] Stereoselective synthesis of threo and erythroβ-hydroxy and β-disubstituted-β-hydroxy α-amino acids [J].

Blaskovich, MA ;

Evindar, G ;

Rose, NGW ;

Wilkinson, S ;

Luo, Y ;

Lajoie, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3631-3646

[8] SYNTHESIS OF A CHIRAL SERINE ALDEHYDE EQUIVALENT AND ITS CONVERSION TO CHIRAL ALPHA-AMINO-ACID DERIVATIVES [J].

BLASKOVICH, MA ;

LAJOIE, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5021-5030

[9] TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN [J].

BOGER, DL ;

PATANE, MA ;

ZHOU, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8544-8556

[10]

CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34

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