The DOI matches its Crossref record; 27 of the 27 references it cites were found in a registry or an index.
Comparing the Enantioselective Power of Steric and Electrostatic Effects in Transition‐Metal‐Catalyzed Asymmetric Synthesis
Abstract
The current approach to improve and tune the enantioselective performances of transition‐metal catalysts for asymmetric synthesis is mostly focused to modifications of the steric properties of the ancillary ligands of the active metal. Nevertheless, it is also known that electrostatic effects can have a remarkable role to promote selectivity in asymmetric synthesis. Using the Rh‐catalyzed asymmetric 1,4‐addition of phenylboronic acid to 2‐cyclohexenone leading to chiral 3‐phenylcyclohexanone as an example, we could show that high enantioselectivity can be indeed achieved using catalysts essentially based either on steric or electrostatic effects as the main source of enantioselective induction. In this contribution we suggest that the analysis of the surface of interaction between the catalyst and the substrate could be a useful tool to quantify the power of steric and electrostatic effects of catalysts.
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Cites
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Cited by
Towards the online computer-aided design of catalytic pockets
Falivene, L., Cao, Z., Petta, A., Serra, L., Poater, A., Oliva, R., Scarano, V., & Cavallo, L. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0319-5 · Cited by 1,290
Self-citationSambVca 2. A Web Tool for Analyzing Catalytic Pockets with Topographic Steric Maps
Falivene, L., Credendino, R., Poater, A., Petta, A., Serra, L., Oliva, R., Scarano, V., & Cavallo, L. (2016) · Organometallics · doi:10.1021/acs.organomet.6b00371 · Cited by 907
Self-citationQuantifying and understanding the steric properties of N-heterocyclic carbenes
Gómez-Suárez, A., Nelson, D. J., & Nolan, S. P. (2017) · Chemical Communications · doi:10.1039/c7cc00255f · Cited by 391
Zahrt, A. F., Athavale, S. V., & Denmark, S. E. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00425 · Cited by 212
Metadata
- Authors
- Poater, A., Ragone, F., Mariz, R., Dorta, R., & Cavallo, L.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2010-11-16
- Volume
- 16
- Issue
- 48
- Pages
- 14348-14353
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2105990795
- Cited by
- 255
- References
- 27
- FWCI
- 5.05
- Type
- journal article
- Language
- en
- Open access
- closed
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