STUDIES ON N-METALLO IMINES - SYNTHESIS OF N-UNSUBSTITUTED AZIRIDINES FROM N-TRIMETHYLSILYL IMINES AND LITHIUM ENOLATES OF ALPHA-HALO ESTERS

被引：52

作者：

CAINELLI, G ^{[1
]}

PANUNZIO, M ^{[1
]}

GIACOMINI, D ^{[1
]}

机构：

[1] ICOCEA,CNR,I-40064 OZZANO EMILIA,ITALY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)71234-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of lithium enolates of 2-halo carboxylic esters to N-trimethylsilyl imines results in the formation of 1H - aziridine derivatives, in the Darzens fashion, with high cis-selectivity.

引用

页码：121 / 124

页数：4

共 23 条

[1] A SYNTHETIC APPROACH TO AZETIDINONES FROM NITRILES AND LITHIUMTRIETHOXYALUMINUM HYDRIDE
ANDREOLI, P
CAINELLI, G
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GIACOMINI, D
MARTELLI, G
PANUNZIO, M
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[2] REACTION OF SILYLIMINES WITH ESTER ENOLATES - SYNTHESIS OF N-UNSUBSTITUTED AZETIDINONES STARTING FROM NITRILES
ANDREOLI, P
CAINELLI, G
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GIACOMINI, D
MARTELLI, G
PANUNZIO, M
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[3] STEREOCONTROLLED TOTAL SYNTHESIS OF THE CHIRAL BUILDING BLOCK (3S,4R)-3-[(R)-1-HYDROXYETHYL]-4-ACETYLOXY-AZETIDIN-2-ONE - A USEFUL SYNTHON FOR THE SYNTHESIS OF (+)-THIENAMYCIN, CARBAPENEMS AND PENEMS
CAINELLI, G
CONTENTO, M
GIACOMINI, D
PANUNZIO, M
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[4] BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5
CAINELLI, G
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GIACOMINI, D
MARTELLI, G
SPUNTA, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6879 - 6880
[5] STEREOSPECIFIC SYNTHESIS OF A CHIRAL INTERMEDIATE FOR THE PREPARATION OF THIENAMYCIN, PENEMS, AND CARBAPENEMS - USE OF THE NITRO-GROUP AS A HYDROXY PROTECTING GROUP
CAINELLI, G
PANUNZIO, M
BASILE, T
BONGINI, A
GIACOMINI, D
MARTELLI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12): : 2637 - 2642
[6] METALLO-IMINES - USEFUL REAGENTS IN ORGANIC-SYNTHESIS
CAINELLI, G
PANUNZIO, M
ANDREOLI, P
MARTELLI, G
SPUNTA, G
GIACOMINI, D
BANDINI, E
[J]. PURE AND APPLIED CHEMISTRY, 1990, 62 (04) : 605 - 612
[7] BETA-LACTAMS FROM ESTERS AND SILYLIMINES - A REVALUATION - SYNTHESIS OF N-UNSUBSTITUTED 4-ALKYL-BETA-LACTAMS
CAINELLI, G
GIACOMINI, D
PANUNZIO, M
MARTELLI, G
SPUNTA, G
[J]. TETRAHEDRON LETTERS, 1987, 28 (44) : 5369 - 5372
[8] CAINELLI G, 1990, J ORG CHEM, V55, P4199
[9] CAINELLI G, 1990, TETRAHEDRON LETT, V46, P3481
[10] CAINELLI G, 1990, IL FARMACO

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