DIASTEREOSELECTIVE BIS-ALKYLATION OF CHIRAL NON-RACEMIC ALPHA,BETA-UNSATURATED GAMMA-LACTAMS

被引:43
作者
BAUSSANNE, I [1 ]
CHIARONI, A [1 ]
HUSSON, HP [1 ]
RICHE, C [1 ]
ROYER, J [1 ]
机构
[1] CNRS,INST CHIM SUBSTANCES NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0040-4039(00)76705-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new chiral non-racemic gamma-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated alpha to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.
引用
收藏
页码:3931 / 3934
页数:4
相关论文
共 15 条
[1]   SYNTHESIS AND STRUCTURE ELUCIDATION OF THE CONDENSATION PRODUCTS BETWEEN THIOPHENE DICARBALDEHYDES AND AROMATIC-AMINES - POTENTIAL ANALGESIC AND ANTI-INFLAMMATORY AGENTS [J].
BENACHENHOU, F ;
MESLI, MA ;
ELBORAI, M ;
HANQUET, B ;
GUILARD, R .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (05) :1531-1534
[2]   REACTIONS OF PHTHALALDEHYDE WITH AMMONIA AND AMINES [J].
DOMINH, T ;
JOHNSON, AL ;
JONES, JE ;
SENISE, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) :4217-4221
[3]   ENANTIOSELECTIVE ALKYLATION OF CHIRAL ENOLATES [J].
EVANS, DA ;
TAKACS, JM .
TETRAHEDRON LETTERS, 1980, 21 (44) :4233-4236
[4]   A SIMPLE ONE-STEP SYNTHESIS OF N-SUBSTITUTED ISOINDOLIN-1-ONES - DIASTEREOFACIALLY SELECTIVE PROTONATION OF AN INTERMEDIATE ISOINDOLINOL [J].
GRIGG, R ;
GUNARATNE, HQN ;
SRIDHARAN, V .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (17) :1183-1184
[5]  
GUERRIER L, 1983, J AM CHEM SOC, V105, P7554
[6]  
LARCHEVEQUE M, 1978, TETRAHEDRON LETT, P3961
[7]   A FACILE SYNTHESIS OF CHIRAL BICYCLIC LACTAMS UTILIZED IN THE FORMATION OF CHIRAL QUATERNARY CARBON-COMPOUNDS [J].
MEYERS, AI ;
LEFKER, BA ;
SOWIN, TJ ;
WESTRUM, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4243-4246
[8]  
MICOUIN L, IN PRESS TETRAHEDRON
[9]   ASYMMETRIC-SYNTHESIS .17. FACILE GENERATION OF A CHIRAL AZOMETHINE YLIDE VIA THE CN(R,S) METHOD [J].
ROUDEN, J ;
ROYER, J ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1989, 30 (38) :5133-5136
[10]  
ROYER J, 1993, HETEROCYCLES, V36, P1493