Synthesis And Diastereoselective Complexation Of Enantiopure Sulfinyl Dienes: The Preparation Of Sulfinyl Iron(0) Dienes
Journal Of Organic Chemistry
The preparation of a diverse array of enantiomerically pure 1- and 2-sulfinyl dienes has been achieved via Stille coupling of halovinyl sulfoxides and vinyl stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of the corresponding sulfinyl diene iron(0) tricarbonyl complexes was accomplished by utilizing Fe(CO)(5)/NMO or (bda)Fe(CO)(3) as iron(0) tricarbonyl transfer reagents. Installation of the iron(0) tricarbonyl fragment was shown to be highly diastereoselective (10-16:1) for (R)-(1Z)-1-sulfinyl dienes, most likely as a result of allylic 1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is also described.
Robert S. Paley; A. De Dios; Lara Ann Estroff , '97; Jennifer Anne Lafontaine , '93; C. Montero; David James McCulley , '96; M. B. Rubio; M. P. Ventura; Heather L. Weers , '94; R. F. De La Pradilla; S. Castro; R. Dorado; and M. Morente.
"Synthesis And Diastereoselective Complexation Of Enantiopure Sulfinyl Dienes: The Preparation Of Sulfinyl Iron(0) Dienes".
Journal Of Organic Chemistry.