ADDITION OF 2-LITHIOFURAN TO CHIRAL ALPHA-ALKOXY NITRONES - A STEREOSELECTIVE APPROACH TO ALPHA-EPIMERIC BETA-ALKOXY-ALPHA-AMINO ACIDS

被引：0

作者：

DONDONI, A ^{[1
]}

JUNQUERA, F ^{[1
]}

MERCHAN, FL ^{[1
]}

MERINO, P ^{[1
]}

TEJERO, T ^{[1
]}

机构：

[1] UNIV ZARAGOZA,CSIC,ICMA,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN

来源：

SYNTHESIS-STUTTGART | 1994年 / 12期

关键词：

NITRONES; HYDROXYAMINES; 2-LITHIOFURAN; BETA-ALKOXY-ALPHA-AMINO ACIDS; ASYMMETRIC SYNTHESIS;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of 2-lithiofuran (1) to the N-benzyl nitrones 2a-d, derived from chiral alpha-alkoxy aldehydes, affords beta-alkoxy-alpha-hydroxyamino-2-alkylfurans in good yields and with syn selectivity. Conversely, the reaction with the same nitrones precomplexed with diethylaluminum chloride leads to the same adducts but with anti selectivity. Three pairs of epimeric hydroxylamines are subjected to reductive N-dehydroxylation with titanium(III) chloride and then to furyl-carboxylic acid conversion with ruthenium tetroxide to give the corresponding alpha-epimeric beta-alkoxy-alpha-amino acids.

引用

页码：1450 / 1456

页数：7

共 4 条

[1] STEREOCONTROL BY DIETHYLALUMINUM CHLORIDE IN THE ADDITION OF 2-LITHIOFURAN AND N-METHYL-2-LITHIOIMIDAZOLE TO ALPHA-ALKOXY NITRONES - TOTAL SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID
DONDONI, A
FRANCO, S
MERCHAN, FL
MERINO, P
TEJERO, T
TETRAHEDRON LETTERS, 1993, 34 (34) : 5479 - 5482
[2] Asymmetric addition of organometallic reagents to chiral alpha-alkoxy hydrazones
Nicaise, O
Denmark, S
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (3-4): : 395 - 398
[3] STEREOSELECTIVE AMINOHOMOLOGATION OF CHIRAL ALPHA-ALKOXY ALDEHYDES VIA THIAZOLE ADDITION TO NITRONES - APPLICATION TO THE SYNTHESIS OF N-ACETYL-D-MANNOSAMINE
DONDONI, A
JUNQUERA, F
MERCHAN, FL
MERINO, P
TEJERO, T
TETRAHEDRON LETTERS, 1992, 33 (29) : 4221 - 4224
[4] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS USING A BETA-ALANINE DERIVATIVE WITH 2 CHIRAL HANDLES
AKSSIRA, M
BOUMZEBRA, M
KASMI, H
ROUMESTANT, ML
VIALLEFONT, P
AMINO ACIDS, 1994, 7 (01) : 79 - 81

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