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Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization

Tiffany Piou, Fedor Romanov-Michailidis, Melissa A. Ashley, Maria Romanova-Michaelides and Tomislav Rovis*

*Department of Chemistry, Columbia University, New York, New York, United States 10027, Email: tr2504columbia.edu

T. Piou, F. Romanov-Michailidis, M. A. Ashley, M. Romanova-Michaelides, T. Rovis, J. Am. Chem. Soc., 2018, 140, 9587-9593.

DOI: 10.1021/jacs.8b04243 (free Supporting Information)


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Abstract

In diastereoselective cyclopropanation of alkenes with N-enoxyphthalimides through rhodium(III) catalysis, a switch from trans- to cis-diastereoinduction is attributed to a mechanistic dichotomy. Selectivity might be determined by the flexibility of rhodacyclic intermediates derived from ring-opened versus -unopened phthalimides.

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Key Words

cyclopropanes


ID: J48-Y2018