STEREOSELECTIVE AMINOHOMOLOGATION OF CHIRAL ALPHA-ALKOXY ALDEHYDES VIA THIAZOLE ADDITION TO NITRONES - APPLICATION TO THE SYNTHESIS OF N-ACETYL-D-MANNOSAMINE

被引：35

作者：

DONDONI, A ^{[1
]}

JUNQUERA, F ^{[1
]}

MERCHAN, FL ^{[1
]}

MERINO, P ^{[1
]}

TEJERO, T ^{[1
]}

机构：

[1] UNIV SARAGOSSA,FAC CIENCIAS,DEPT QUIM ORGAN,ZARAGOZA,SPAIN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 29期

关键词：

THIAZOLE; NITRONES; AMINO ALDEHYDES; AMINO SUGARS;

D O I：

10.1016/S0040-4039(00)74694-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of 2-lithiothiazole to nitrones derived from D-glyceraldehyde and D-arabinose affords anti-adducts from which alpha-amino aldehydes are revealed by thiazole-to-formyl deblocking. The methodology provides a new synthesis of N-acetyl D-mannosamine and D-mannosamine hydrochloride.

引用

页码：4221 / 4224

页数：4

共 7 条

[1] NEW CHIRAL AUXILIARY FOR THE STEREOSELECTIVE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY ALDEHYDES
CHARETTE, AB
ROUILLARD, L
MALENFANT, E
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 86 - ORGN
[2] ADDITION OF 2-LITHIOFURAN TO CHIRAL ALPHA-ALKOXY NITRONES - A STEREOSELECTIVE APPROACH TO ALPHA-EPIMERIC BETA-ALKOXY-ALPHA-AMINO ACIDS
DONDONI, A
JUNQUERA, F
MERCHAN, FL
MERINO, P
TEJERO, T
SYNTHESIS-STUTTGART, 1994, (12): : 1450 - 1456
[3] DESIGN OF NEW CHIRAL AUXILIARIES FOR THE STEREOSELECTIVE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY ALDEHYDES - A REMARKABLE REMOTE PROTECTING GROUP EFFECT
CHARETTE, AB
MELLON, C
ROUILLARD, L
MALENFANT, E
SYNLETT, 1993, (01) : 81 - 82
[4] HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS
BANFI, L
BERNARDI, A
COLOMBO, L
GENNARI, C
SCOLASTICO, C
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20): : 3784 - 3790
[5] HIGHLY STEREOSELECTIVE SE' ADDITIONS OF ALPHA-ALKOXY ALLYLSTANNANES TO CHIRAL ALDEHYDES - SYNTHESIS OF A C-1-C-9 SUBUNIT OF TYLONOLIDE
MARSHALL, JA
YASHUNSKY, DV
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19): : 5493 - 5495
[6] Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate
Casero, F
Cipolla, L
Lay, L
Nicotra, F
Panza, L
Russo, G
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10): : 3428 - 3432
[7] 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

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