Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids
- Morrill, Louis C.
- Smith, Samuel M.
- Slawin, Alexandra M. Z.
- Smith, Andrew D.
DOIAbstract
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
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