Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles

Abstract

Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. sydowii CBMAI 935 promoted the reduction of 2-azido-1-phenylethanones 1–4 with high selectivities to yield the (S)-2-azido-1-phenylethanols 1a–4a. Bioreduction of compounds 1–4 by M. racemosus CBMAI 847 led to (R)-2-azido-1-phenylethanols for 1, 2 and 4 and (S)-2-azido-1-phenylethanol 3. Enantiomerically enriched 2-azido-1-phenylethanols 1a–4a and phenylacetylene 5 were applied in the synthesis of β-hydroxy-1,2,3-triazoles using CuSO₄ and sodium ascorbate leading to regioselective formation of enantioenriched 1,4-disubstituted 1,2,3-triazole compounds 1b–4b.

Keywords:

• Arylazides
• 1,2,3-triazoles
• biocatalysis
• microorganisms
• click reaction

Disclosure statement

The authors report no declarations of interest. The authors alone are responsible for the content and writing of the paper.

Additional information

Funding

N. Alvarenga thanks the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for scholarship (141844/2013-2). A.L.M. Porto thanks the CNPq (400202/2014-0 and 301987/2013-0) and the Fundação de Amparo à Pesquisa do Estado de São Paulo (2014/18257-0) for financial support.