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Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides
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Arokianathar, Jude N., Hartley, Will C., McLaughlin, Calum, Greenhalgh, Mark D., Stead, Darren, Ng, Sean, Slawin, Alexandra M. Z. and Smith, Andrew D. (2021) Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides. Molecules, 26 (21). 6333. doi:10.3390/molecules26216333 ISSN 1420-3049.
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WRAP-Isothiourea-catalyzed-enantioselective-α-alkylation-esters-via-1,6-conjugate-addition-para-quinone-methides-Greenhalgh-2021.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution 4.0. Download (1299Kb) | Preview |
Official URL: http://dx.doi.org/10.3390/molecules26216333
Abstract
The isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides is reported. para-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, is proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products can be isolated, or derivatized in situ by addition of benzylamine to give amides at up to 99% yield. Although low diastereocontrol is observed, the diastereoisomeric ester products are separable and formed with high enantiocontrol (up to 94:6 er).
| Item Type: | Journal Article | |||||||||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Engineering > WMG (Formerly the Warwick Manufacturing Group) | |||||||||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Catalysts, Intermediates (Chemistry) , Organic compounds -- Synthesis, Electrophiles, Alkylation | |||||||||||||||||||||||||||
| Journal or Publication Title: | Molecules | |||||||||||||||||||||||||||
| Publisher: | M D P I AG | |||||||||||||||||||||||||||
| ISSN: | 1420-3049 | |||||||||||||||||||||||||||
| Official Date: | 20 October 2021 | |||||||||||||||||||||||||||
| Dates: |
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| Volume: | 26 | |||||||||||||||||||||||||||
| Number: | 21 | |||||||||||||||||||||||||||
| Article Number: | 6333 | |||||||||||||||||||||||||||
| DOI: | 10.3390/molecules26216333 | |||||||||||||||||||||||||||
| Status: | Peer Reviewed | |||||||||||||||||||||||||||
| Publication Status: | Published | |||||||||||||||||||||||||||
| Access rights to Published version: | Open Access (Creative Commons) | |||||||||||||||||||||||||||
| Date of first compliant deposit: | 30 November 2021 | |||||||||||||||||||||||||||
| Date of first compliant Open Access: | 3 December 2021 | |||||||||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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