INTRAMOLECULAR CYCLOPROPANATION - STEREOSPECIFIC SYNTHESIS OF (E)-1-AMINOCYCLOPROPANE-1-CARBOXYLIC AND (Z)-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACIDS

被引：50

作者：

KOSKINEN, AMP

MUNOZ, L

机构：

[1] Department of Chemistry, University of Oulu, Linnanmaa

[2] Departamento de Quimica Pura y Aplicada, Universidad de Vigo, Galicia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 04期

关键词：

D O I：

10.1021/jo00056a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields. The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclo[3.1.0]hexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively. The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40% overall from malonic acid) The free amino acids 12 and 18 can be liberated in two steps.

引用

收藏

页码：879 / 886

页数：8

相关论文

共 100 条

[1] ON THE BIOSYNTHESIS OF ETHYLENE [J].

ADLINGTON, RM ;

APLIN, RT ;

BALDWIN, JE ;

RAWLINGS, BJ ;

OSBORNE, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (18) :1086-1087

[2] ON THE STEREOCHEMISTRY OF ETHYLENE BIOSYNTHESIS [J].

ADLINGTON, RM ;

BALDWIN, JE ;

RAWLINGS, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) :290-292

[3] 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

[4] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1839-1844

[5] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T ;

YONEYOSHI, Y ;

NAGASE, T .

TETRAHEDRON LETTERS, 1982, 23 (06) :685-688

[6] REACTION OF 4-METHYLENE-5(4H)-OXAZOLONES WITH DIAZOMETHANE [J].

ARENAL, I ;

BERNABE, M ;

ALVAREZ, EF ;

IZQUIERDO, ML ;

PENADES, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :607-613

[7] A CONVENIENT SYNTHESIS OF REGIO-SPECIFICALLY 2-ALKYLATED-3-DEUTERIATED-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACIDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

RAWLINGS, BJ .

TETRAHEDRON LETTERS, 1985, 26 (04) :481-484

[8] ON THE BIOSYNTHESIS OF ETHYLENE - DETERMINATION OF THE STEREOCHEMICAL COURSE USING MODIFIED SUBSTRATES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

LAJOIE, GA ;

RAWLINGS, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (21) :1496-1498

[9] 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

[10] STEREOSPECIFIC INACTIVATION OF THE GENERAL ACYL-COA DEHYDROGENASE FROM PIG-KIDNEY BY (R)-(-)-(METHYLENECYCLOPROPYL)ACETYL-COA AND (S)-(+)-(METHYLENECYCLOPROPYL)ACETYL-COA [J].

BALDWIN, JE ;

OSTRANDER, RL ;

SIMON, CD ;

WIDDISON, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :2021-2022

← 1 2 3 4 5 6 7 8 9 10 →