Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531, Smith, Samuel M., Slawin, Alexandra M. Z. and Smith, Andrew D. 2014. Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids. Journal of Organic Chemistry 79 (4) , pp. 1640-1655. 10.1021/jo402591v

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Abstract

Isothiourea HBTM-2.1 promotes the catalytic asymmetric α-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	0022-3263
Last Modified:	28 Oct 2022 09:22
URI:	https://orca.cardiff.ac.uk/id/eprint/74293

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