Highly enantioselective reduction with novel, bridged NADH models

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Abstract

Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.

Original languageEnglish
Pages (from-to)1207-1211
Number of pages5
JournalAngewandte Chemie - International Edition in English
Volume36
Issue number11
Publication statusPublished - 1997
Externally publishedYes

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Keywords

  • Asymmetric synthesis
  • Macrocycles
  • NADH model compounds
  • Pyridinophanes

ASJC Scopus subject areas

  • Chemistry(all)

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