Diastereoselective reduction of β-ketophosphonates derived from amino acids.: A new entry to enantiopure β-hydroxy-γ-aminophosphonate derivatives

被引：32

作者：

Ordóñez, M ^{[1
]}

de la Cruz, R ^{[1
]}

Fernández-Zertuche, M ^{[1
]}

Muñoz-Hernández, MA ^{[1
]}

机构：

[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 62210, Morelos, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(02)00159-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reduction of gamma-N,N-dibenzylamino-beta-ketophosphonates 4 derived from readily available (S)-tribenzylated amino acids teas achieved with catecholborane at -20degreesC affording gamma-amino-beta-hydroxyphosphonates 5 in high diastereoselectivity and good chemical yield. These reactions provide a new entry to enantiomerically pure gamma-amino-beta-hydroxyphosphonates. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：559 / 562

页数：4

共 28 条

[1] Diastereoselective reduction of dimethyl γ-[(N-p-toluenesulfonyl)amino]-β-ketophosphonates derived from amino acids
Ordóñez, M
De la Cruz-Cordero, R
Fernández-Zertuche, M
Muñoz-Hernández, MA
García-Barradas, O
TETRAHEDRON-ASYMMETRY, 2004, 15 (19) : 3035 - 3043
[2] A new diastereoselective approach to the synthesis of α-hydroxy-β-amino acids based on the frame of captodative olefins
Herrera, R
Jiménez-Vázquez, HA
Tamariz, J
ARKIVOC, 2005, : 233 - 249
[3] Stereoselective sodium borohydride reduction, catalyzed by manganese(II) chloride, of γ-oxo-α-amino acids.: A practical approach to syn-γ-hydroxy-α-amino acids
Berkes, D
Kolarovic, A
Povazanec, F
TETRAHEDRON LETTERS, 2000, 41 (27) : 5257 - 5260
[4] A new class of chiral diimine ligands derived from amino acids.
Morgan, RJ
Dillon, J
Morgan, O
Donovan, RJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1025 - U1025
[5] Preparation of New α-Hydroxy Acids Derived from Amino Acids and Their Corresponding Polyesters
Cohen-Arazi, Naomi
Katzhendler, Jeoshua
Kolitz, Michal
Domb, Abraham I.
MACROMOLECULES, 2008, 41 (20) : 7259 - 7263
[6] Diastereoselective Strecker reaction of imines derived from D-glyceraldehyde. A new route to QQ -hydroxy-a-amino acids
Tetrahedron Lett, 16 (2859):
[7] Convenient entry to α-amino-β-hydroxy-γ-methyl carboxylic acids.: Diastereoselective formation and directed homogeneous hydrogenation of 3-(3-aryl-1-hydroxy-2-methylprop-2-enyl)-1,4-benzodiazepin-2-ones
Hamersak, Z
Gaso, D
Kovac, S
Hergold-Brundic, A
Vickovic, I
Sunjic, V
HELVETICA CHIMICA ACTA, 2003, 86 (06) : 2247 - 2257
[8] Ziroconium-mediated, highly diastereoselective ring contraction of vinylmorpholine derivatives from α-amino acids. An application to the synthesis of (-)-macronecine
1600, (116):
[9] DIASTEREOSELECTIVE STRECKER REACTION OF IMINES DERIVED FROM D-GLYCERALDEHYDE - A NEW ROUTE TO BETA-HYDROXY-ALPHA-AMINO ACIDS
CATIVIELA, C
DIAZDEVILLEGAS, MD
GALVEZ, JA
TETRAHEDRON LETTERS, 1995, 36 (16) : 2859 - 2860
[10] Stereoselective synthesis of beta-amino alcohols: diastereoselective reduction of chiral alpha'-amino enones derived from amino acids
Chung, SK
Kang, DN
TETRAHEDRON-ASYMMETRY, 1997, 8 (18) : 3027 - 3030

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