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Synthesis of Chiral Nonracemic α‑Difluoromethylthio Compounds with Tetrasubstituted Stereogenic Centers via a Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation
journal contribution
posted on 2018-11-08, 18:19 authored by Hiroya Kondo, Mayaka Maeno, Kenta Sasaki, Ming Guo, Masaru Hashimoto, Motoo Shiro, Norio ShibataThe synthesis of
chiral, nonracemic difluoromethylthio (SCF2H) compounds
that contain a tetrasubstituted stereogenic center
is reported. Racemic α-SCF2H-β-ketoallylesters 5 were initially prepared by an electrophilic difluoromethylthiolation
of β-ketoallylesters 6, followed by a Pd-catalyzed
Tsuji decarboxylative asymmetric allylic alkylation (DAAA) to provide
a wide variety of chiral, nonracemic α-allyl-α-SCF2H-ketones (4) with high enantiopurity. This strategy
can be extended to the enantioselective synthesis of chiral, nonracemic
α-allyl-α-trifluoromethylthio(SCF3)-ketones
(7).
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nonracemic α- allyl -α-SCF 2 H-ketoneselectrophilic difluoromethylthiolationTetrasubstituted Stereogenic CentersRacemic α- SCF 2 H -β-ketoallylesters 5tetrasubstituted stereogenic centerβ- ketoallylesters 6Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylationnonracemic difluoromethylthioenantioselective synthesischiralPd-catalyzed Tsuji decarboxylativeDAAAallylic alkylationSCF 2 H
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