Abstract

A two-step stereoselective chemoenzymatic synthesis of optically active ?-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of ?-, ? -, and ? -chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells screened (baker's yeast, Kluyveromyces marxianus CBS 6556, Saccharomyces cerevisiae CBS 7336, Lactobacillus reuteri DSM 20016), baker's yeast was the one providing the best yields and the highest enantiomeric ratios (up to 95:5 er) in the bioreduction of the above ketones. The obtained optically active chlorohydrins could be almost quantitatively cyclized in a basic medium into the corresponding ?-aryl-substituted cyclic ethers without any erosion of their enantiomeric integrity. In this respect, valuable, chiral non-racemic functionalized oxygen containing heterocycles (e.g., (S)-styrene oxide, (S)-2-phenyloxetane, (S)-2-phenyltetrahydrofuran), amenable to be further elaborated on, can be smoothly and successfully generated from their prochiral precursors.

Autore Pugliese

• Cardellicchio Cosimo

Tutti gli autori

• Vitale P.; Digeo A.; Perna F.M.; Agrimi G.; Salomone A.; Scilimati A.; Cardellicchio C.; Capriati V.

Titolo volume/Rivista

Catalysts

Anno di pubblicazione

2017

ISSN

2073-4344

ISBN

Non Disponibile

Numero di citazioni Wos

Nessuna citazione

Ultimo Aggiornamento Citazioni

Non Disponibile

Numero di citazioni Scopus

Non Disponibile

Ultimo Aggiornamento Citazioni

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Settori ERC

Non Disponibile

Codici ASJC

Non Disponibile