THERMAL REARRANGEMENT OF ENANTIOENRICHED ALPHA-HYDROXY IMINES .1. ENANTIOCONTROLLED SYNTHESIS OF ALPHA-SUBSTITUTED ALPHA-AMINO KETONES

被引：24

作者：

COMPAIN, P ^{[1
]}

GORE, J ^{[1
]}

VATELE, JM ^{[1
]}

机构：

[1] UNIV LYON 1,CNRS,CHIM ORGAN LAB 1,F-69622 VILLEURBANNE,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 23期

关键词：

D O I：

10.1016/0040-4039(95)00680-B

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioenriched 2-allyl- and 2-(3-trimethylsilypropargyl)-2-hydroxycyclohexanone were respectively obtained by resolution from the corresponding diastereomeric acetal derived from C-2-symmetrical diol or from the camphanate ester. Study of the rearrangement of their corresponding imine derivatives has shown that it occurred with complete retention of the stereogenicity.

引用

页码：4059 / 4062

页数：4

共 20 条

[1] OXIDATION OF EPOXIDES BY DIMETHYL SULFOXIDE - A SIMPLE SYNTHESIS OF ALPHA-HYDROXY KETONES
COHEN, T
TSUJI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) : 1681 - &
[2] COMPAIN P, 1994, J SYNLETT, P943
[3] DALY JW, 1982, PROGR CHEM ORGANIC N, V41, P205
[4] ENANTIOSELECTIVE SYNTHESIS OF OXA-SPIRO COMPOUNDS
DESMAELE, D
DANGELO, J
[J]. TETRAHEDRON LETTERS, 1989, 30 (03) : 345 - 348
[5] ELIEL EL, 1944, STEREOCHEMISTRY ORGA, P1080
[6] FUJISAWA T, 1984, CHEM LETT, P2055, DOI 10.1246/cl.1984.2055
[7] GRAWRONSKI JK, 1987, J AM CHEM SOC, V109, P6726
[8] KEPPENS M, 1994, SYNLETT, P255
[9] A TOTAL SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE TERREIN (TRANS-4,5-DIHYDROXY-3-[(E)-1-PROPENYL]-2-CYCLOPENTEN-1-ONE)
KOLB, HC
HOFFMANN, HMR
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (04) : 237 - 250
[10] PREPARATION OF AUXILIARIES FOR ASYMMETRIC SYNTHESES FROM TARTARIC ACID - ADDITIONS OF BUTYLLITHIUM TO ALDEHYDES IN CHIRAL MEDIA
SEEBACH, D
KALINOWSKI, HO
BASTANI, B
CRASS, G
DAUM, H
DORR, H
DUPREEZ, NP
EHRIG, V
LANGER, W
NUSSLER, C
OEI, HA
SCHMIDT, M
[J]. HELVETICA CHIMICA ACTA, 1977, 60 (02) : 301 - 325

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