Chiral Auxiliary-Bearing Isocyanides as Synthons: Synthesis of Strongly Fluorescent (+)-5-(3,4-Dimethoxyphenyl)-4-[[N- [(4S)-2-oxo-4-(phenylmethyl)-2-oxazolidinyl]]carbonyl]oxazole and Its Enantiomer.

JianS. Tang, JohnG. Verkade

Index: J. Org. Chem. 61(25) , 8750-8754, (1996)

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Abstract

Both (4S-(+)-3-(isocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (R)-1 and its enantiomer (S)-1 have been synthesized as potentially useful synthons in asymmetric synthesis. Optically active (+)-5-(3,4-dimethoxyphenyl)-4-[[N-[(4S)-2-oxo-4-(phenylmethyl)-2-oxazolidinyl]]carbonyl] oxazole (S)-2 and its enantiomer (R)-2 obtained by treating 3,4-dimethoxybenzoyl chloride with (S)-1 and (R)-1, respectively, in the presence of the nonionic superbase P(MeNCH(2)CH(2))(3)N, have high fluorescence quantum yields. The molecular structure of (S)-2 obtained by X-ray means is also presented.