Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 4, Pages 1640-1655Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402591v
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Funding
- Royal Society for a University Research Fellowship
- Carnegie Trust for the Universities of Scotland
- European Research Council under the European Union [279850]
- Engineering and Physical Sciences Research Council [1634601] Funding Source: researchfish
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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.
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