Tetrahedron

Baker's yeast reduction of prochiral γ-nitroketones: Enantioselective synthesis of (S)-4-nitroalcohols

A Guarna, EG Occhiato, LM Spinetti, ME Vallecchi…

Index: Guarna, Antonio; Occhiato, Ernesto G.; Spinetti, Laura M.; Vallecchi, Maria E.; Scarpi, Dina Tetrahedron, 1995 , vol. 51, # 6 p. 1775 - 1788

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Citation Number: 21

Abstract

The baker's yeast reduction of seven different prochiral nitroketones 1a-g occurred on the re face of the carbonyl group, thus affording the (S)-nitroalcohols 2a-g, with different level of enantioselectivity (ee 15–99%). The best results (ee= 99%) were achieved when the substituent R is markedly different from the nitroalkyl group [eg 1a (R= Me) and 1e (R= o- MeO-C6H4)]. The ee and the configuration of the bioproducts were assigned by NMR ...