The baker's yeast reduction of 5-nitro-2,8-nonanedione 2 afforded the corresponding (2S,8S)-5-nitro-2,8-nonanediol3 with complete diastereoselectivity and high enantioselectivity. The conversion of 3 into the thermodynamic (E,E)/(Z,Z) (3:1) mixture of optically active (95% e.e.) 2,7-dimethyl-1,6-dioxaspiro[4.4]nonanes 5 was then achieved by spontaneous cyclization under the acidic conditions of the Nef reaction.
Baker's yeast reduction of prochiral g-nitro ketones. II. Straightforward enantioselective synthesis of 2,7-dimethyl-1,6-dioxaspiro[4.4]nonanes / E. OCCHIATO; A. GUARNA; F. DE SARLO; D. SCARPI. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 6:(1995), pp. 2971-2976. [10.1016/0957-4166(95)00394-0]
Baker's yeast reduction of prochiral g-nitro ketones. II. Straightforward enantioselective synthesis of 2,7-dimethyl-1,6-dioxaspiro[4.4]nonanes
OCCHIATO, ERNESTO GIOVANNI;GUARNA, ANTONIO;DE SARLO, FRANCESCO;SCARPI, DINA
1995
Abstract
The baker's yeast reduction of 5-nitro-2,8-nonanedione 2 afforded the corresponding (2S,8S)-5-nitro-2,8-nonanediol3 with complete diastereoselectivity and high enantioselectivity. The conversion of 3 into the thermodynamic (E,E)/(Z,Z) (3:1) mixture of optically active (95% e.e.) 2,7-dimethyl-1,6-dioxaspiro[4.4]nonanes 5 was then achieved by spontaneous cyclization under the acidic conditions of the Nef reaction.
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