Synthesis of Chiral Nonracemic α‑Difluoromethylthio
Compounds with Tetrasubstituted Stereogenic Centers via a Palladium-Catalyzed
Decarboxylative Asymmetric Allylic Alkylation
Posted on 2018-11-08 - 18:19
The 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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Kondo, Hiroya; Maeno, Mayaka; Sasaki, Kenta; Guo, Ming; Hashimoto, Masaru; Shiro, Motoo; et al. (2018). Synthesis of Chiral Nonracemic α‑Difluoromethylthio
Compounds with Tetrasubstituted Stereogenic Centers via a Palladium-Catalyzed
Decarboxylative Asymmetric Allylic Alkylation. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b02998
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AUTHORS (7)
HK
Hiroya Kondo
MM
Mayaka Maeno
KS
Kenta Sasaki
MG
Ming Guo
MH
Masaru Hashimoto
MS
Motoo Shiro
NS
Norio Shibata
KEYWORDS
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