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Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids.

ABSTRACT: The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diastereoselectivity. Preliminary results show similar efficiency in the preparation of indanes. This new method is used in the first enantioselective synthesis of an oligoresveratrol natural product (E-δ-viniferin).

SUBMITTER: Soldi C

PROVIDER: S-EPMC4227726 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids.

Soldi Cristian C Lamb Kellan N KN Squitieri Richard A RA González-López Marcos M Di Maso Michael J MJ Shaw Jared T JT

Journal of the American Chemical Society 20141021 43

The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diastereoselectivity. Preliminary results show similar efficiency in the preparation of indanes. This new method is used in the first enantioselective synthesis of an oligoresveratrol natural product (E-δ-viniferin). ...[more]

PMID: 25308822

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