Catalytic properties of 4,5-bridged proline methano- and ethanologues in the Hajos–Parrish intramolecular aldol reaction
Literature Information
Publication Date
2021-12-15
DOI
10.1039/D1QO01688A
Impact Factor
5.281
Authors
Sofiane Hocine, Gilles Berger, K. N. Houk, Stephen Hanessian
View Original
Abstract
The catalysis of the Hajos–Parrish reaction by cis- and trans-4,5-ethano-proline was explored experimentally and computationally with DFT (ωB97X-D and MN15) and DLPNO-CCSD(T). Both of the new catalysts are as active as proline or cis- and trans-4,5-methano-proline, with the trans-ethano-proline being as enantioselective as proline. A thorough theoretical analysis of the electronic factors influencing catalysis is reported.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
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8.7%
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724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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