ASYMMETRIC SYNTHESES OF ALL 4 STEREOISOMERS OF 2,3-METHANOMETHIONINE

被引：76
作者：
BURGESS, K
HO, KK
机构：
[1] Chemistry Department, Texas A & M University, College Station
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 22期
关键词：
D O I：
10.1021/jo00048a028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine ((Z)- and (E)-cyclo-Met) are described. The source of chirality in these reactions is the trifluoromethylsulfonate ester 1b which reacts with di-tert-butyl malonate via direct displacement of trifluoromethylsulfonate followed by lactonization to give 1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo[3.1.0]hexane (2). Conversion of compound 2 into (Z)-cyclo-Met can be achieved via ring opening of the lactone, Hoffmann rearrangement, mesylation, and displacement with thiomethoxide. A route to (E)-cyclo-Met was developed using a lipase to effect a critical ester hydrolysis.
引用
收藏
页码：5931 / 5936
页数：6
相关论文
共 53 条
[1]   ASYMMETRIC-SYNTHESIS .16. ENANTIOMERICALLY PURE SUBSTITUTED CYCLOPROPANE AMINO-ACID PRECURSORS VIA THE CN(R,S) METHOD [J].
AITKEN, DJ ;
ROYER, J ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1988, 29 (27) :3315-3318
[2]   ASYMMETRIC-SYNTHESIS BY THE CN(R,S) METHOD .19. ASYMMETRIC-SYNTHESIS OF 2,3-METHANOHOMOSERINE - A GENERAL-APPROACH TO CHIRAL 2-SUBSTITUTED CYCLOPROPANE AMINO-ACIDS [J].
AITKEN, DJ ;
ROYER, J ;
HUSSON, HP .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2814-2820
[3]   ASYMMETRIC-SYNTHESIS OF CIS AND TRANS-2-METHYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS AND 2-ETHYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS [J].
ALAMI, A ;
CALMES, M ;
DAUNIS, J ;
ESCALE, F ;
JACQUIER, R ;
ROUMESTANT, ML ;
VIALLEFONT, P .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :175-178
[4]  
BACH ACI, 1983, 8TH PEPT STRUCT FUNC, P299
[5]   THE RESOLUTION OF RACEMIC 2-ALKYL-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACIDS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
RAWLINGS, BJ ;
JONES, RH .
TETRAHEDRON LETTERS, 1985, 26 (04) :485-488
[6]   USE OF (S)-(TRIFLOXYMETHYL)OXIRANE IN THE SYNTHESIS OF A CHIRAL BETA-ADRENOCEPTOR ANTAGONIST, (R) AND (S)-9-[[3-(TERT-BUTYLAMINO)-2-HYDROXYPROPYL]OXIMINO]FLUORENE [J].
BALDWIN, JJ ;
MCCLURE, DE ;
GROSS, DM ;
WILLIAMS, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (08) :931-936
[7]  
BERNABE M, 1979, EUR J MED CHEM, V14, P33
[8]   HETERO-SUBSTITUTED METHYLIDENEOXAZOLONES - 2,3-METHANOHOMOSERINE AND METHANOMETHIONINE SYNTHESIS [J].
BLAND, J ;
SHAH, A ;
BORTOLUSSI, A ;
STAMMER, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :992-995
[9]   ENZYME-INHIBITION BY ELECTROPHILIC CYCLOPROPANE DERIVATIVES [J].
BRECKENRIDGE, RJ ;
SUCKLING, CJ .
TETRAHEDRON, 1986, 42 (20) :5665-5677
[10]   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
123456