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Baker's yeast reduction of prochiral γ-nitroketones. II.1straightforward enantioselective synthesis of 2,7-dimethyl-1,6-dioxaspiro[4.4]nonanes

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
12
Identifiers
DOI: 10.1016/0957-4166(95)00394-0
Disciplines
  • Physics

Abstract

Abstract The baker's yeast reduction of 5-nitro-2,8-nonanedione 2 afforded the corresponding (2 S,8 S)-5-nitro-2,8-nonanediol 3 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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