DYNAMIC KINETIC RESOLUTION BY STEREOSPECIFIC AMINATION UTILIZING 2-OXOIMIDAZOLIDINE-4-CARBOXYLATE AS A NOVEL CHIRAL AUXILIARY

被引：25

作者：

NUNAMI, KI

KUBOTA, H

KUBO, A

机构：

[1] Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co. Ltd., Yodogawa-ku, Osaka, 532, 16-89

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)78458-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel type of dynamic kinetic resolution by stereospecific amination was exploited utilizing 2-oxoimidazolidine-4-carboxylate 1 as a chiral auxiliary. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate (2) with benzylamine in HMPA in the presence of K2CO3 or Et(3)N at 25 degrees C predominantly afforded tert-butyl (4S)-1-methyl-3-((2R)-2-benzylaminopropionyl)-2-oxoimidazolidine-4-carboxylate ((S,R)-4) in nearly quantitative yield.

引用

页码：8639 / 8642

页数：4

共 16 条

[1] ABSOLUTE ASYMMETRIC SYNTHESIS .1. ON MECHANISM OF PHOTOCHEMICAL SYNTHESIS OF NONRACEMIC HELICENES WITH CIRCULARLY POLARIZED-LIGHT - WAVELENGTH DEPENDENCE OF OPTICAL YIELD OF OCTAHELICENE
BERNSTEI.WJ
CALVIN, M
BUCHARDT, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) : 494 - &
[2] ASYMMETRIC BROMINATION OF ALKENES IN PRESENCE OF CINCHONA ALKALOIDS
BERTI, G
MARSILI, A
[J]. TETRAHEDRON, 1966, 22 (09) : 2977 - &
[3] SUBSTRATE AND STERIC SPECIFICITY OF HYDROPYRIMIDINE HYDRASE
CECERE, F
GALLI, G
MORISI, F
[J]. FEBS LETTERS, 1975, 57 (02) : 192 - 194
[4] FULLING G, 1987, J AM CHEM SOC, V109, P2845
[5] CHEMOENZYMATIC ASYMMETRIC-SYNTHESIS OF AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYZES OF 2-PHENYL-OXAZOLIN-5-ONES
GU, RL
LEE, IS
SIH, CJ
[J]. TETRAHEDRON LETTERS, 1992, 33 (15) : 1953 - 1956
[6] CHIRAL (BETA-AMINOALKYL)PHOSPHINES - HIGHLY EFFICIENT PHOSPHINE-LIGANDS FOR CATALYTIC ASYMMETRIC GRIGNARD CROSS-COUPLING
HAYASHI, T
KONISHI, M
FUKUSHIMA, M
KANEHIRA, K
HIOKI, T
KUMADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) : 2195 - 2202
[7] LIPASE-CATALYZED KINETIC RESOLUTION WITH INSITU RACEMIZATION - ONE-POT SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN ACETATES FROM ALDEHYDES
INAGAKI, M
HIRATAKE, J
NISHIOKA, T
ODA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9360 - 9361
[8] QUANTITATIVE EXPRESSION OF DYNAMIC KINETIC RESOLUTION OF CHIRALLY LABILE ENANTIOMERS - STEREOSELECTIVE HYDROGENATION OF 2-SUBSTITUTED 3-OXO CARBOXYLIC ESTERS CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES
KITAMURA, M
TOKUNAGA, M
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) : 144 - 152
[9] DYNAMIC KINETIC RESOLUTION IN BINAP-RUTHENIUM(II) CATALYZED HYDROGENATION OF 2-SUBSTITUTED 3-OXO CARBOXYLIC ESTERS
KITAMURA, M
OHKUMA, T
TOKUNAGA, M
NOYORI, R
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (01) : 1 - 4
[10] MATHEMATICAL TREATMENT OF KINETIC RESOLUTION OF CHIRALLY LABILE SUBSTRATES
KITAMURA, M
TOKUNAGA, M
NOYORI, R
[J]. TETRAHEDRON, 1993, 49 (09) : 1853 - 1860

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