SYNTHESIS OF CIS-DELTA-PHENYLMETHYL-D-PROLINE USING A NITROGEN-CENTERED RADICAL DERIVED FROM A CHIRAL OXAZIRIDINE

被引：12

作者：

AUBE, J

GULGEZE, B

PENG, X

机构：

[1] Department of Medicinal Chemistry University of Kansas, Lawrence

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1994年 / 4卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(01)80410-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Oxaziridines react with Cu(I) salts to afford products resulting from the initial formation of a nitrogen-centered radical/oxygen-centered anion pair. For an alpha-aryl radical, a chiral pyrrolidine was obtained with high enantioselectivity and was transformed into cis-delta-phenylmethyl-D-proline. 3-Carbomethoxy- or 3-(2'-furyl)-substitution gave products resulting from beta-cleavage or C-->N migration, respectively.

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页码：2461 / 2464

页数：4

相关论文

共 25 条

[1] A DIVERGENT ROUTE TOWARD LACTAM-BASED DIPEPTIDYL BUILDING-BLOCKS [J].

AUBE, J ;

WOLFE, MS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (09) :925-928

[2] NEW COPPER(I)-CATALYZED REACTIONS OF OXAZIRIDINES - STEREOCHEMICAL CONTROL OF PRODUCT DISTRIBUTION [J].

AUBE, J ;

PENG, X ;

WANG, YG ;

TAKUSAGAWA, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5466-5467

[3] SYNTHETIC ASPECTS OF AN ASYMMETRIC NITROGEN-INSERTION PROCESS - PREPARATION OF CHIRAL, NON-RACEMIC CAPROLACTAMS AND VALEROLACTAMS - TOTAL SYNTHESIS OF (-)-ALLOYOHIMBANE [J].

AUBE, J ;

WANG, YG ;

HAMMOND, M ;

TANOL, M ;

TAKUSAGAWA, F ;

VANDERVELDE, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4879-4891

[4] BETA-LACTAM SYNTHESIS USING ORGANOIRON INTERMEDIATES - PREPARATION OF 3-CARBOMETHOXYCARBAPENAM [J].

BERRYHILL, SR ;

PRICE, T ;

ROSENBLUM, M .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02) :158-162

[5] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[6] SYNTHESIS AND MOLECULAR GEOMETRY OF HEXAMERIC TRIPHENYLPHOSPHINOCOPPER(I) HYDRIDE AND CRYSTAL-STRUCTURE OF H6CU6(PPH3)6.HCONME2 [J].

CHURCHILL, MR ;

BEZMAN, SA ;

OSBORN, JA ;

WORMALD, J .

INORGANIC CHEMISTRY, 1972, 11 (08) :1818-+

[7] A NEW APPROACH TO POLYPROPIONATES - ROUTES TO SUBUNITS OF MONENSIN AND TIRANDAMYCIN [J].

DANISHEFSKY, S ;

HARVEY, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (23) :6647-6652

[8] STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES [J].

DANISHEFSKY, SJ ;

DENINNO, MP ;

CHEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3929-3940

[9] HEATS OF FORMATION OF ACETYL HALIDES AND OF ACETYL RADICAL [J].

DEVORE, JA ;

ONEAL, HE .

JOURNAL OF PHYSICAL CHEMISTRY, 1969, 73 (08) :2644-&

[10] THE PREPARATION AND PROPERTIES OF OXAZIRANES [J].

EMMONS, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (21) :5739-5754