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Paper | Special issue | Vol 37, No. 1, 1994, pp.529-539
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S49
Asymmetric Synthesis of a Homochiral Δ2-Isoxazoline Amino Acid Derivative

Bernadette M. Kelly-Basetti, Maureen F. Mackay, Suzanne M. Pereira, G. Paul Savage,* and Gregory W. Simpson

*CSIRO, Divisuon of Chemicals & Polymers, Private Bag 10, Rosebank MDC, Clayton Vic. 3169, Austalia

Abstract

(2R)-4Methylene-2-phenyl-3-propionyloxazolidin-5-one underwent 1,3-dipolar cycloaddition with 2,6-dichlorobenzonitrile oxide to give (5S,7R)-3-(2,6-diphenyI)-7-phenyl-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.