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

Cristian Soldi, Kellan N. Lamb, Richard A. Squitieri, Marcos González-López, Michael J. Di Maso, Jared T. Shaw

Research output: Contribution to journalArticle

71 Citations (Scopus)

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).

Original languageEnglish (US)
Pages (from-to)15142-15145
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number43
DOIs
StatePublished - Oct 29 2014

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Biological Products
Metals
Electrons
Enantioselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Soldi, C., Lamb, K. N., Squitieri, R. A., González-López, M., Di Maso, M. J., & Shaw, J. T. (2014). Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids. Journal of the American Chemical Society, 136(43), 15142-15145. https://doi.org/10.1021/ja508586t

Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids. / Soldi, Cristian; Lamb, Kellan N.; Squitieri, Richard A.; González-López, Marcos; Di Maso, Michael J.; Shaw, Jared T.

In: Journal of the American Chemical Society, Vol. 136, No. 43, 29.10.2014, p. 15142-15145.

Research output: Contribution to journalArticle

Soldi, C, Lamb, KN, Squitieri, RA, González-López, M, Di Maso, MJ & Shaw, JT 2014, 'Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids', Journal of the American Chemical Society, vol. 136, no. 43, pp. 15142-15145. https://doi.org/10.1021/ja508586t
Soldi C, Lamb KN, Squitieri RA, González-López M, Di Maso MJ, Shaw JT. Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids. Journal of the American Chemical Society. 2014 Oct 29;136(43):15142-15145. https://doi.org/10.1021/ja508586t
Soldi, Cristian ; Lamb, Kellan N. ; Squitieri, Richard A. ; González-López, Marcos ; Di Maso, Michael J. ; Shaw, Jared T. / Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 43. pp. 15142-15145.
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