Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids
Abstract
Isothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-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.
Citation
Morrill , L C , Smith , S M , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids ' , The Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1640-1655 . https://doi.org/10.1021/jo402591v
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
ISSN
0022-3263Type
Journal article
Description
This work is supported by funding from the Carnegie Trust for the Universities of Scotland (L.C.M.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC Grant Agreement No. 279850.Collections
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