ChemInform Abstract: Stereoselective Synthesis of Cyclopropanes via Homoallylic Participation.

Abstract

Stereoselective Synthesis of Cyclopropanes via Homoallylic Participation. -A stereospecific synthesis of difunctionalized cyclopropanes like (III) is described. Several nucleophiles, e.g. (II), (IV) and (VI), are used for quenching the triflation/cyclization of the alcohol (I) leading to interesting functionalities at the α-position of the cyclopropyl ring. The addition of triethylamine leads to elimination products, e.g. (VIII). Et3N is also used for the synthesis of the chiral ketone (XII), a reminiscent of the subunit in ambruticin. -(NAGA-SAWA, T.; HANDA, Y.; ONOGUCHI, Y.; OHBA, S.; SUZUKI, K.; Synlett (1995) 7, 739-741; Dep. Chem., Keio Univ., Hiyoshi, Yokohama 223, Japan; EN)