Memory of chirality in the enantioselective synthesis of β-lactams derived from amino acids.: Influence of the reaction conditions

被引：0
|
作者：
Bonache, MA
Gerona-Navarro, G
Martín-Martínez, M
García-López, MT
López, P
Cativiela, C
González-Muñiz, R
机构：
[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain
[2] Univ Zaragoza, CSIC, ICMA, Dept Quim Organ, E-50009 Zaragoza, Spain
来源：
SYNLETT | 2003年 / 07期
关键词：
amino acids; memory of chirality; beta-lactams; enantioselectivity; AN solvent-depedency;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric induction observed during cyclisation of N-benzyl-N-chloroacetyl-(L)-Phe derivatives to the corresponding S-enriched 2-azetidinones, ascribed to chirality memory, can be controlled by the appropriate choice of the base and solvent. Using the organic base BTPP, the ee values obtained in different solvents showed a good correlation with the AN solvent parameter, except for NMP. It seems that a combination of the solvent properties, rather than individual parameters, and the presence of enolate aggregates are decisive for final enantiomer distribution.
引用
收藏
页码：1007 / 1011
页数：5
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