Efficient preparation of enantiomerically pure (E)-4-(tributylstannanyl)but-3-en-2-ol via lipase-mediated resolution |
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| Institution: | 1. Institute of Microbiology, Technische Universität Braunschweig, Spielmannstrasse 7, 38106 Braunschweig, Germany;2. Department of Molecular Structural Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany;3. Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany;4. Department of Biotechnology, University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan |
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| Abstract: | The practical preparation of enantiomerically pure (E)-4-(tributylstannanyl)but-3-en-2-ol 1 from 3-butyn-2-ol 2 is reported. A modified Guibé's Pd-catalyzed hydrostannation of 2 provided the racemic γ-hydroxy vinylstannane 1 in a good yield. The enzymatic esterification of 1, with an inexpensive lipozyme, afforded (R)-3 and (S)-1 with very high enantiomeric excesses and chemical yields. This procedure is suitable for the multigram scale preparation of the potential chiral building blocks, (R)-1 and (S)-1. |
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