Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: Improved reactivity and stereochemical outcome

Vadim A. Soloshonok, Chaozhong Cai, Victor J Hruby

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Abstract

Application of the (N-trans-enoyl)oxazolidines as Michael acceptors in the kinetically controlled additions with a Ni(II)-complex of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone 1 was shown to be synthetically advantageous over the alkyl enoylates, allowing for remarkable improvement in reactivity and, in most cases, diastereoselectivity of the reactions. While the stereochemical outcome of the Michael additions of the aliphatic (N-trans-enoyl)oxazolidines with complex 1 depended on the steric bulk of the alkyl group on the starting oxazolidines, the diastereoselectivity of the aromatic (N-trans-enoyl)oxazolidines reactions was found to be controlled by the electronic properties of the aryl ring. In particular, the additions of complex 1 with (N-cinnamoyl)oxazolidines, bearing electron-withdrawing substituents on the phenyl ring, afforded the (2S,3R)-configured products with synthetically useful selectivity and in quantitative chemical yield, thus allowing an efficient access to sterically constrained β-substituted pyroglutamic acids and related compounds. (C) 1999 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)4265-4269
Number of pages5
JournalTetrahedron Asymmetry
Volume10
Issue number22
DOIs
Publication statusPublished - Nov 19 1999

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ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

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