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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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Official URL: http://dx.doi.org/10.3390/molecules26216333

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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
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:
DateEvent
20 October 2021Published
14 October 2021Accepted
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:
Project/Grant IDRIOXX Funder NameFunder ID
FP7/2007- 2013Seventh Framework Programmehttp://dx.doi.org/10.13039/100011102
279850European Research Councilhttp://dx.doi.org/10.13039/501100000781
UNSPECIFIEDAstraZenecahttp://dx.doi.org/10.13039/100004325
EP/M506631/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
UNSPECIFIEDSyngenta Internationalhttp://dx.doi.org/10.13039/501100010761
CRITICAT, EP/L016419/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
EP/M508214/1 [EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
Wolfson Research Merit AwardRoyal Societyhttp://dx.doi.org/10.13039/501100000288

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