ASYMMETRIC ALDOL ADDITION-REACTIONS OF A CHIRAL 3-SULFONYL-1,3-OXAZOLIDINE-MASKED LITHIUM 2-FORMYLCYCLOHEXANONE ENOLATE

被引:15
作者
HOPPE, I
HOPPE, D
HERBSTIRMER, R
EGERT, E
机构
[1] UNIV KIEL,DEPT ORGAN CHEM,OLSHAUSENSTR 40,W-2300 KIEL 1,GERMANY
[2] UNIV GOTTINGEN,INST ANORGAN CHEM,W-3400 GOTTINGEN,GERMANY
[3] UNIV FRANKFURT,INST ORGAN CHEM,W-6000 FRANKFURT,GERMANY
关键词
D O I
10.1016/S0040-4039(00)97190-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound, prepared by kinetically controlled deprotonation of a stereohomogeneous 2-(2-oxocyclohexyl)-1,3-oxazolidine, undergoes highly anti-stereoselective aldol addition with alkanals. © 1990.
引用
收藏
页码:6859 / 6862
页数:4
相关论文
共 14 条
[1]  
[Anonymous], 1989, ANGEW CHEM, V101, P65
[2]   NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS [J].
BERNARDI, A ;
CARDANI, S ;
CARUGO, O ;
COLOMBO, L ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON LETTERS, 1990, 31 (19) :2779-2782
[3]   ALLYLIC STEREOCENTER DIRECTED CYCLOPROPANATION - A NEW HIGHLY ENANTIOSELECTIVE SYNTHESIS OF HEMICARONIC ALDEHYDE [J].
BERNARDI, A ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3733-3734
[4]   ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION OF CUPRATES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE - ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-4-BENZYLOXYBUTANAL AND 2-ALKYL-4-OXOPENTANAL [J].
CARDANI, S ;
POLI, G ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON, 1988, 44 (18) :5929-5938
[5]   ASYMMETRIC-SYNTHESIS OF 3,4-CIS-SUBSTITUTED BETA-LACTAMS VIA CHIRAL NOREPHEDRINE-DERIVED OXAZOLIDINES [J].
CARDANI, S ;
GENNARI, C ;
SCOLASTICO, C ;
VILLA, R .
TETRAHEDRON, 1989, 45 (23) :7397-7404
[6]  
CONDEFRIEBOES K, 1990, SYNLETT, P99
[7]  
DUBOIS JE, 1967, TETRAHEDRON LETT, P4215
[8]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111
[9]   3-ARYLSULFONYLOXAZOLIDINES AS CHIRAL TEMPLATES - ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED 2-HYDROXYCYCLOHEXANECARBALDEHYDES FROM 2-HYDROXYMETHYLENECYCLOHEXANONE [J].
HOPPE, I ;
HOPPE, D ;
WOLFF, C ;
EGERT, E ;
HERBST, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01) :67-69
[10]   TRANSITION STRUCTURES FOR THE ALDOL REACTIONS OF ANIONIC, LITHIUM, AND BORON ENOLATES [J].
LI, Y ;
PADDONROW, MN ;
HOUK, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :481-493