Synthesis of Chiral Pyrrolidine Derivatives from (S)-Pyroglutamic Acid. II. 4-(Hydroxymethyl)-3-azabicyclo[3.1.0]hexan-2-ones and 5, 5-Disubstituted 2-Pyrrolidinones

Tatsuo NAGASAKA; Tomoko IMAI

doi:10.1248/cpb.45.36

Tatsuo NAGASAKA, Tomoko IMAI

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Keywords: (S)-pyroglutamic acid, chiral pyrrolidine, 5, 5-disubstituted 2-pyrrolidinone, azabicyclo[3.1.0]hexane, unsaturated lactam, N, O-acetal

JOURNAL FREE ACCESS

1997 Volume 45 Issue 1 Pages 36-42

DOI https://doi.org/10.1248/cpb.45.36

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Abstract

The chiral pyrrolidine derivatives, 4-(hydroxymethyl)-3-azabicyclo[3.1.0]hexan-2-ones (10 and 11) and 5, 5-disubstituted 2-pyrrolidinones (20, 21 and 22), were synthesized starting from (S)-pyroglutamic acid and absolute configuration determination was made based on the ¹H-NMR spectra of the bicyclic lactam intermediates.

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