Synfacts 2009(12): 1401-1401  
DOI: 10.1055/s-0029-1218210
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Hydroxylations of Benzylic C-H Bonds Using Biocatalysis

Contributor(s): Benjamin List, Kristina Zumbansen
Y. Chen, F. Lie, Z. Li*
National University of Singapore, Singapore
Further Information

Publication History

Publication Date:
20 November 2009 (online)


A highly enantioselective benzylic hydroxylation of benzene derivatives containing reactive functional groups employing resting cells of Pseudomonas monteilii TA-5 as a biocatalyst is reported. Based on experimental results it is suggested that an NADH- or NADPH-dependent monooxygenase in the resting cells is responsible for the benzylic hydroxylation. The synthetic utility of this transformation is demonstrated by conducting it on a 0.8 mmol scale where benzylic alcohol 2 was obtained in 56% yield with a slightly decreased enantiomeric ratio of 97:3. Remarkably products 1 and 3 are the first examples of enan­tioselective benzylic hydroxylations of these substrates.