Enantioselective addition of Grignard reagents to a 2-thiazolyl nitrone

被引：29

作者：

Merchan, FL

Merino, P

Rojo, I

Tejero, T

Dondoni, A

机构：

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

[2] UNIV FERRARA,DIPARTIMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 03期

关键词：

D O I：

10.1016/0957-4166(96)00060-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The addition of organomagnesium compounds to the N-benzyl 2-thiazolyl nitrone 1 in the presence of various chiral additives and Lewis acids leads to hydroxylamines 2 in moderate to good enantiomeric excess (up to 74%); the reductive dehydroxylation of these compounds affords enantioenriched alpha-amino 2-alkylthiazoles 3 in good yields (76-66%). (C) 1996 Elsevier Science Ltd

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页码：667 / 670

页数：4

相关论文

共 34 条

[1] ADDITION OF ORGANOMETALLIC REAGENTS TO N-GLYCOSYL NITRONES - ENANTIOSELECTIVE SYNTHESES OF (+)-(R)-ZILEUTON AND (-)-(S)-ZILEUTON [J].

BASHA, A ;

HENRY, R ;

MCLAUGHLIN, MA ;

RATAJCZYK, JD ;

WITTENBERGER, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :6103-6106

[2] ENANTIOSELECTIVE SYNTHESIS OF PRIMARY AMINES VIA GRIGNARD ADDITIONS TO STEREOGENIC N-(ALPHA-PHENYL-BETA-(BENZYLOXY)ETHYL)NITRONES [J].

CHANG, ZY ;

COATES, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3475-3483

[3] DIASTEREOSELECTIVITY OF ORGANOMETALLIC ADDITIONS TO NITRONES BEARING STEREOGENIC N-SUBSTITUENTS [J].

CHANG, ZY ;

COATES, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3464-3474

[4] NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID [J].

CICCHI, S ;

HOLD, I ;

BRANDI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5274-5275

[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[6] ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].

DENMARK, SE ;

NAKAJIMA, N ;

NICAISE, OJC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798

[7]

DONDONI A, 1994, SYNTHESIS-STUTTGART, P1450

[8] SYNTHESIS OF N-BENZYL NITRONES [J].

DONDONI, A ;

FRANCO, S ;

JUNQUERA, F ;

MERCHAN, F ;

MERINO, P ;

TEJERO, T .

SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550

[9]

DONDONI A, 1992, NEW ASPECTS ORGANIC, V2, P105

[10]

DONDONI A, 1992, MODERN SYNTHETIC MET, P377

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