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Highly enantio- and diastereoselective reduction of sulfur-functionalized cyclic ketones with baker's yeast

✍ Scribed by Tamotsu Fujisawa; Kengo Yamanaka; Bingidimi I. Mobele; Makoto Shimizu

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
175 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

Bakers' yeast reduction of 2-phenylthiocyclopentanone, 2-phenylthiocyclohexanone, and 2phenylthio-2-cyclopentenone affords the corresponding (lS,2R)-2-phenylthiocycloalkanols in optically pure form and excellent diastereomeric excess. Cyclic P-phenylthiocycloalkanols possess potentially versatile properties as building blocks due to the characteristic features of sulfur atom1 and will constitute a valuable class of synthons for the specific construction of natural products involving forskolin.2 However, hitherto no method has been available for the preparation of 2-arylthiocycloalkanols in optically pure form. The only reported examples involve asymmetric ring opening of cyclopentene oxide and cyclohexene oxide with thiols catalyzed by zinc and manganese d-tartrates as heterogeneous chiral Lewis acid catalysts, in which the optical purity dose not exceed 85%.3 Bakers' yeast (Saccharomyces cerevisiae) has been used as a convenient reducing reagent to produce chiral secondary alcohols of high enantiomeric excess from various functionalized ketones. 4 We wish to report herein the bakers' yeast

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