NaHMDS/B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-promoted diastereoselective Friedel-Crafts alkylation of indoles/pyrroles with <i>N-tert</i>-butanesulfinylimines: towards the asymmetric synthesis of bisindole alkaloid Calcicamide B.
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ABSTRACT: This study proposed an innovative and pragmatic approach to the asymmetric Friedel-Crafts reaction by employing indoles/pyrroles and chiral N-tert-butanesulfinylimines promoted by NaHMDS/B(C6F5)3. This method effectively produces enantioenriched α-(3-indolyl)glycine and α-(2-pyrrolyl)glycine derivatives, which can be readily transformed into the crucial chiral diamine skeletons. The first successful asymmetric total synthesis of marine-derived anti-tumor bisindole alkaloid Calcicamide B was achieved by employing this reaction as a crucial chiral control step.
SUBMITTER: Zhang G
PROVIDER: S-EPMC12593423 | biostudies-literature | 2025 Nov
REPOSITORIES: biostudies-literature
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