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.
|ジャーナル||Angewandte Chemie - International Edition in English|
|出版ステータス||Published - 1997 1月 1|
ASJC Scopus subject areas
- 化学 (全般)