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

页码：1007 / 1011

页数：5

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