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Article: Diastereo- and Enantioselective Construction of Stereochemical Arrays Exploiting Non-Classical Hydrogen Bonding in Enolborates
Title | Diastereo- and Enantioselective Construction of Stereochemical Arrays Exploiting Non-Classical Hydrogen Bonding in Enolborates |
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Authors | |
Keywords | Copper DFT calculations Enantioselective Hydrogen bonding Spirocycles |
Issue Date | 30-Jun-2024 |
Publisher | Wiley |
Citation | Chemistry - A European Journal, 2024, v. 30, n. 46 How to Cite? |
Abstract | We report a copper-catalyzed reductive aldol addition to aldehydes and ketones, with pinacolborane as stoichiometric reductant, that results in the generation of stereodefined syn-aldol products. Cyclic, acyclic, fused and spirocyclic aldols bearing contiguous stereocenters are obtained with excellent yields and diastereoselectivities. Moreover, enantioselective reactions could be carried out with cycloalkenones to deliver aldols bearing three contiguous stereocenters and with up to 98 % ee. Computations reveal that the enolborate intermediate undergoes the syn-aldol reaction via a twist-boat transition state that is stabilized by non-classical hydrogen bonding interactions. |
Persistent Identifier | http://hdl.handle.net/10722/347383 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
DC Field | Value | Language |
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dc.contributor.author | Li, Tin Lok Matthew | - |
dc.contributor.author | Scheeff, Stephan | - |
dc.contributor.author | Chen, Jiahua | - |
dc.contributor.author | Johnston, Ryne C. | - |
dc.contributor.author | Rizzo, Antonio | - |
dc.contributor.author | Krenske, Elizabeth H. | - |
dc.contributor.author | Chiu, Pauline | - |
dc.date.accessioned | 2024-09-23T00:30:14Z | - |
dc.date.available | 2024-09-23T00:30:14Z | - |
dc.date.issued | 2024-06-30 | - |
dc.identifier.citation | Chemistry - A European Journal, 2024, v. 30, n. 46 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/347383 | - |
dc.description.abstract | We report a copper-catalyzed reductive aldol addition to aldehydes and ketones, with pinacolborane as stoichiometric reductant, that results in the generation of stereodefined syn-aldol products. Cyclic, acyclic, fused and spirocyclic aldols bearing contiguous stereocenters are obtained with excellent yields and diastereoselectivities. Moreover, enantioselective reactions could be carried out with cycloalkenones to deliver aldols bearing three contiguous stereocenters and with up to 98 % ee. Computations reveal that the enolborate intermediate undergoes the syn-aldol reaction via a twist-boat transition state that is stabilized by non-classical hydrogen bonding interactions. | - |
dc.language | eng | - |
dc.publisher | Wiley | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | Copper | - |
dc.subject | DFT calculations | - |
dc.subject | Enantioselective | - |
dc.subject | Hydrogen bonding | - |
dc.subject | Spirocycles | - |
dc.title | Diastereo- and Enantioselective Construction of Stereochemical Arrays Exploiting Non-Classical Hydrogen Bonding in Enolborates | - |
dc.type | Article | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.1002/chem.202401485 | - |
dc.identifier.scopus | eid_2-s2.0-85199906129 | - |
dc.identifier.volume | 30 | - |
dc.identifier.issue | 46 | - |
dc.identifier.eissn | 1521-3765 | - |
dc.identifier.issnl | 0947-6539 | - |