22218-99-1Relevant academic research and scientific papers
Surprising fenchone induced cyclization: Synthesis of the new chiral diol biphenyl-2,2′-sulfone-3,3′-bisfenchol (BISFOL)
Soki, Francis,Neud?rfl, J?rg M.,Goldfuss, Bernd
, p. 10449 - 10453 (2005)
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.
