1346159-07-6Relevant academic research and scientific papers
Polarity inversion of donor-acceptor cyclopropanes: Disubstituted δ-lactones via enantioselective iridium catalysis
Moran, Joseph,Smith, Austin G.,Carris, Ryan M.,Johnson, Jeffrey S.,Krische, Michael J.
, p. 18618 - 18621 (2011)
The coupling of carbonyl electrophiles at the donor position of donor-acceptor cyclopropanes is described, representing an inversion of polarity with respect to conventional reactivity modes displayed by these reagents. Specifically, upon exposure of donor-acceptor cyclopropanes to alcohols in the presence of a cyclometalated iridium catalyst modified by (S)-BINAP, catalytic C-C coupling occurs, providing enantiomerically enriched products of carbonyl allylation. Identical products are obtained upon isopropanol-mediated transfer hydrogenation of donor-acceptor cyclopropanes in the presence of aldehydes. The reaction products are directly transformed to cis-4, 5-disubstituted δ-lactones.
