Chiral and flexible 2,4-pentanediol-tethered cyclopropanation of olefins with a carbenoid derived from a diazo ester to construct three stereogenic centers

Abstract 2,4-Pentanediol-tethered cyclopropanation of an olefin with an internal carbenoid generated from a diazo ester proceeded smoothly to give a chiral adduct having three stereogenic centers under full stereocontrol. The high stereoselectivity was not affected by the structure of the olefinic portion, studied so far with six substrates. Conversion of the product cyclopropane to other optically active compounds is also reported.