Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

Article abstract of DOI:10.1016/0957-4166(96)00389-8

The microbial reduction of β-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic β-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed.