STEREOSELECTIVE EPOXIDATION OF CHIRAL ELECTRON-POOR GAMMA-AMINOOLEFINS

被引：33

作者：

REETZ, MT

LAUTERBACH, EH

机构：

[1] Fachbereich Chemie der Universität, 3550 Marburg, Hans-Meerwein-Strasse

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

AMINO ACIDS; GAMMA-AMINOOLEFINS; EPOXIDATION; DIASTEREOSELECTIVITY;

D O I：

10.1016/0040-4039(91)80016-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral alpha,beta-unsaturated compounds 3 and 8, prepared from amino acids 1, undergo stereoselective epoxidation reactions using tBuOOH/KOtBu in THF/NH3.

引用

页码：4477 / 4480

页数：4

共 25 条

[1] 1,4-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BEARING A GAMMA-STEREOCENTER - A MOLECULAR MECHANICS MODEL FOR STERIC INTERACTIONS IN THE TRANSITION-STATE
BERNARDI, A
CAPELLI, AM
GENNARI, C
SCOLASTICO, C
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (01) : 21 - 32
[2] Coppola GM, 1987, ASYMMETRIC SYNTHESIS
[3] ON THE CONFIGURATIONAL STABILITY OF ALPHA-PHENYLSELENO-ALKYL-LITHIUM COMPOUNDS
HOFFMANN, RW
JULIUS, M
OLTMANN, K
[J]. TETRAHEDRON LETTERS, 1990, 31 (51) : 7419 - 7422
[4] INFLUENCE OF THE N-PROTECTING GROUP ON THE STEREOCHEMICAL COURSE OF (4 + 2) CYCLO-ADDITION OF 1-ETHOXY-3-[(TRIMETHYLSILYL)OXY]BUTA-1,3-DIENE TO ALPHA-AMINO ALDEHYDES
JURCZAK, J
GOLEBIOWSKI, A
RACZKO, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2495 - 2496
[5] STEREOCONTROLLED CONVERGENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES BY THE REACTION OF ALPHA-AMINO ALDEHYDE WITH ALKOXYTITANIUM HOMOENOLATES
KANO, S
YOKOMATSU, T
SHIBUYA, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (02) : 233 - 236
[6] MARTENS J, 1984, TOP CURR CHEM, V125, P165
[7] STEREOSELECTIVE SYNTHESES OF ERYTHRO-BETA-AMINO AND THREO-BETA-AMINO ALCOHOL DERIVATIVES VIA HETERO-DIELS-ALDER REACTIONS
MIDLAND, MM
AFONSO, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4368 - 4371
[8] MIKAMI K, 1990, TETRAHEDRON LETT, V31, P3909
[9] LANTHANIDES IN ORGANIC-SYNTHESIS .4. REDUCTION OF ALPHA,BETA-EPOXY KETONES WITH SAMARIUM DIIODIDE - A ROUTE TO CHIRAL, NONRACEMIC ALDOLS
MOLANDER, GA
HAHN, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) : 2596 - 2599
[10] Posner G. H., 1975, ORG REACT, V22

← 1 2 3 →