VERSATILE ROUTES TO CHIRAL 4-SUBSTITUTED 2-OXAZOLIDINONES AND α-AMINO ACIDS. USE OF CHIRON, [4+2] CYCLOADDUCTS OF DIALKYL AZODICARBOXYLATES AND 2-OXAZOLONES

Hirofumi MATSUNAGA; Tadao ISHIZUKA; Nobuhiro MARUBAYASHI; Takehisa KUNIEDA

doi:10.1248/cpb.40.1077

Hirofumi MATSUNAGA, Tadao ISHIZUKA, Nobuhiro MARUBAYASHI, Takehisa KUNIEDA

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Keywords: 2-oxazolone, azodicarboxylate, [4+2] cycloaddition, deacylation, chiral synthon, organocuprate, 2-aminoalcohol, 2-oxazolidinone, α-amino acid

JOURNAL FREE ACCESS

1992 Volume 40 Issue 4 Pages 1077-1079

DOI https://doi.org/10.1248/cpb.40.1077

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Abstract

The thermal reaction of 3-[(1S)-2-alkoxyl-1-apocamphanecarbonyl]-2-oxazolones with dialkyl azodicarboxylates results in exclusive formation of [4+2] type cycloadducts with moderate levels of diastereofacial selection, which serve as versatile chiral synthons for a wide variety of 4-alkyl and 4-aryl-2-oxazolidinones as well as α-amino acids.

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