Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids.
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.
EaStCHEM, School of Chemistry, University of St Andrews , North Haugh, St Andrews, KY16 9ST, U.K.
Louis C
LC
Morrill
Samuel M
SM
Smith
Alexandra M Z
AM
Slawin
Andrew D
AD
Smith