Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 46, Pages 15213-15216Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809344
Keywords
asymmetric synthesis; C-H insertion; diastereoselectivity; enantioselectivity; rhodium carbenes
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Funding
- National Institute Of General Medical Sciences of the National Institutes of Health [R01GM124234]
- UC Davis
- National Science Foundation [CHE-1531193]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM124234] Funding Source: NIH RePORTER
- Division Of Chemistry [1531193] Funding Source: National Science Foundation
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We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C-H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C-H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.
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