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Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

Morrill, Louis C. ORCID:, 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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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: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 28 Oct 2022 09:22

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