F. Soki, J. Neudörfl, B. Goldfuss
Oct 31, 2005
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract The new chiral diol BISFOL (biphenyl-2,2′-sulfone-3,3′-bisfenchol) is surprisingly formed by cyclization of diphenylsulfone after treatment with n-buthyllithium at −78 °C and subsequent addition of (−)-fenchone. Formation of fenchyl alcohol as byproduct points to a Meisenheimer intermediate as primary cyclization product, which transfers lithium hydride yielding the cyclic sulfone. As a chiral and chelating ligand, BISFOL catalyzes enantioselective diorganozinc additions to aldehydes and forms with dimethylzinc an unprecedented, macrocyclic, dimeric methylzinc complex.