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
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
收藏
页码:4059 / 4062
页数:4
相关论文
共 20 条
[1]   OXIDATION OF EPOXIDES BY DIMETHYL SULFOXIDE - A SIMPLE SYNTHESIS OF ALPHA-HYDROXY KETONES [J].
COHEN, T ;
TSUJI, T .
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 [J].
DESMAELE, D ;
DANGELO, 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) [J].
KOLB, HC ;
HOFFMANN, HMR .
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 [J].
SEEBACH, D ;
KALINOWSKI, HO ;
BASTANI, B ;
CRASS, G ;
DAUM, H ;
DORR, H ;
DUPREEZ, NP ;
EHRIG, V ;
LANGER, W ;
NUSSLER, C ;
OEI, HA ;
SCHMIDT, M .
HELVETICA CHIMICA ACTA, 1977, 60 (02) :301-325