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In summary, we describe here an eco-compatible chemoenzy-
matic synthesis of thiols, some of which from renewable sources,
involving the sequential intervention of InIII-catalysis and lipase-
catalysis. The InIII-catalysed step provided adducts of olefins and
thioacetic acid in good yields, and the lipase-catalysed solvolysis
showed the best efficiency with primary thioesters, secondary
and tertiary presenting lower yields of thiols. Increased steric hin-
drance in the vicinity of the thioester function also resulted in low-
er yields. The influence of the class and the substitution of the
substrate suggest that interfacial activation of the lipases by med-
ium engineering4 could be helpful to overcome this moderate
activity, and would deserve substrate specific optimisation. Opti-
mised biocatalyst for improved stereopreference would be the next
step forward.
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Acknowledgements
R.B. is grateful to the ERASMUS—IMAGEEN program for a doc-
toral fellowship. This project was supported by the CNRS and the
University of Nice—Sophia Antipolis.
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Supplementary data
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