SYNTHESIS OF 2-[N-(9-PHENYLFLUOREN-9-YL)AMINO]-1-INDANONES BY ANIONIC CYCLIZATION OF PHENYLALANINE-DERIVED OXAZOLIDINONES

被引：29

作者：

PALEO, MR

CASTEDO, L

DOMINGUEZ, D

机构：

[1] UNIV SANTIAGO,FAC QUIM,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN

[2] CSIC,SECC ALCALOIDES,E-15706 SANTIAGO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 10期

关键词：

D O I：

10.1021/jo00062a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel preparation of N-(phenylfluorenyl)-2-amino-1-indanones is described. The key step is the cyclization of aryl-substituted o-bromophenylalanine-derived oxazolidinones with n-BuLi by halogen-metal exchange followed by in situ intramolecular acylation of the aryllithium intermediate. When this method was applied to an optically pure oxazolidinone derived from an amino acid, cyclization occurred with complete retention of the integrity of the chiral center.

引用

页码：2763 / 2767

页数：5

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