A CYCLIZATION REACTION OF METHYL (4R)-3-(2-DIAZO-3-OXOBUTANOYL)THIAZOLIDINE-4-CARBOXYLATE WHICH PROCEEDS WITH RETENTION OF CONFIGURATION, PROBABLY VIA A PLANAR ESTER ENOLATE INTERMEDIATE POSSESSING AXIAL CHIRALITY

被引：31

作者：

BEAGLEY, B

BETTS, MJ

PRITCHARD, RG

SCHOFIELD, A

STOODLEY, RJ

VOHRA, S

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

[2] ICI PHARMACEUT PLC,DEPT CHEM 1,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 14期

关键词：

D O I：

10.1039/c39910000924

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Under basic conditions, the title compound 1b is converted into methyl (6S)-3-acetyl-2-oxo-8-thia-1,4,5-triazabicyclo[4.3.0]non-3-ene-6-carboxylate 4a, the absolute configuration of which is established by X-ray crystallography.

引用

页码：924 / 925

页数：2

共 8 条

[1]

Cram D. J., 1965, FUNDAMENTALS CARBANI

[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[3] 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

[4] SYNTHESIS AND CATALYTIC REACTIONS OF CHIRAL N-(DIAZOACETYL)OXAZOLIDONES [J].

DOYLE, MP ;

DOROW, RL ;

TERPSTRA, JW ;

RODENHOUSE, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1663-1666

[5] DIRECT INTRODUCTION OF DIAZO FUNCTION IN ORGANIC SYNTHESIS [J].

HENDRICKSON, JB ;

WOLF, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (09) :3610-+

[6] ALLYLIC STRAIN IN 6-MEMBERED RINGS [J].

JOHNSON, F .

CHEMICAL REVIEWS, 1968, 68 (04) :375-+

[7] The action of formaldehyde upon cysteine [J].

Ratner, S ;

Clarke, HT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :200-206

[8]

SUNBERG RJ, 1985, J ORG CHEM, V50, P425

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