HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THREO OR ERYTHRO AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS

被引：105

作者：

BARLUENGA, J ^{[1
]}

BARAGANA, B ^{[1
]}

CONCELLON, JM ^{[1
]}

机构：

[1] UNIV OVIEDO,CSIC,INST QUIM ORGANOMETAL ENRIQUE MOLES,E-33071 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期

关键词：

D O I：

10.1021/jo00126a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.

引用

页码：6696 / 6699

页数：4

共 31 条

[1] STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES
ALBECK, A
PERSKY, R
[J]. TETRAHEDRON, 1994, 50 (21) : 6333 - 6346
[2] IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES
ALBECK, A
PERSKY, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) : 653 - 657
[3] RENIN INHIBITORS CONTAINING C-TERMINI DERIVED FROM MERCAPTOHETEROCYCLES
ASHTON, WT
CANTONE, CL
MEURER, LC
TOLMAN, RL
GREENLEE, WJ
PATCHETT, AA
LYNCH, RJ
SCHORN, TW
STROUSE, JF
SIEGL, PKS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) : 2103 - 2112
[4] HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE
ASKIN, D
WALLACE, MA
VACCA, JP
REAMER, RA
VOLANTE, RP
SHINKAI, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2771 - 2773
[5] THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES
BARLUENGA, J
BARAGANA, B
ALONSO, A
CONCELLON, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) : 969 - 970
[6] BARLUENGA J, 1993, TETRAHEDRON LETT, V31, P4563
[7] Behrens C. H., 1983, ALDRICHIM ACTA, V16, P67
[8] BROOK MA, 1983, SYNTHESIS-STUTTGART, P201
[9] BUHLMAYER P, 1988, J MED CHEM, V31, P1839
[10] OPTIMIZATION AND INVIVO EVALUATIONS OF A SERIES OF SMALL, POTENT, AND SPECIFIC RENIN INHIBITORS CONTAINING A NOVEL LEU-VAL REPLACEMENT
DELLARIA, JF
MAKI, RG
BOPP, BA
COHEN, J
KLEINERT, HD
LULY, JR
MERITS, I
PLATTNER, JJ
STEIN, HH
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) : 2137 - 2144

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