ASYMMETRIC-SYNTHESIS OF A HOMOCHIRAL DELTA-2-ISOXAZOLINE AMINO-ACID DERIVATIVE

被引：0

作者：

KELLYBASETTI, BM ^{[1
]}

MACKAY, MF ^{[1
]}

PEREIRA, SM ^{[1
]}

SAVAGE, GP ^{[1
]}

SIMPSON, GW ^{[1
]}

机构：

[1] LA TROBE UNIV,DEPT CHEM,BUNDOORA,VIC 3083,AUSTRALIA

来源：

HETEROCYCLES | 1994年 / 37卷 / 01期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2R)-4-Methylene-2-phenyl-3-propionyloxazolidin-5-one underwent 1,3-dipolar cycloaddition with 2,6-dichlorobenzonitrile oxide to give (5S,7R)-3(2,6-diphenyl)-7-phenyl-6-propionyl-2,6-propionyl-2,6-diaza-1,8-dioxaspiro[4.4]non-2-en-9-one, a protected isoxazoline amino acid. The reaction proceeded regiospecifically and with high stereoselectivity. The anti addition product predominated. The regiochemistry of addition was determined by nmr and the stereochemistry of addition was determined by X-ray analysis. The transition state energies for syn and anti addition were calculated using the semi-empirical AM1 method in the MOPAC package.

引用

页码：529 / 539

页数：11

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