Diastereoselective intramolecular pinacol couplings of sulfinyl iron(0) diene complexes.
3-(2-Formylaryl)-1-sulfinyl-(1Z,3E)-pentadien-5-al iron tricarbonyl complexes were prepared to examine the feasibility and diastereoselectivity of intramolecular pinacol couplings on such substrates. It was found that the pinacol coupling, promoted by VCl(3) x (THF)(3)/Zn, proceeded in good yield and with high diastereoselectivity (>23:1 dr), provided the 2-formylaryl unit remained unsubstituted at the aryl C3 position (ortho to the formyl group). In these latter cases the pinacol coupling was diastereorandom. A 3-formyl-4-(2-formylaryl)-1-sulfinyl-(1Z,3E)-butadiene iron tricarbonyl complex also underwent diastereoselective pinacol coupling (22:1 dr). 3-(3-Formylindolyl)-1-sulfinyl-(1Z,3E)-pentadien-5-al iron tricarbonyl complexes were also prepared, though pinacol coupling of these substrates proceeded in, at best, modest yield for two of the four examples tested. All cases described herein represent the first intramolecular pinacol couplings performed on the periphery of an iron(0) diene tricarbonyl complex.
Paley
Robert S
RS
Department of Chemistry and Biochemistry, Swarthmore College, 500 College Ave., Swarthmore, Pennsylvania 19081, USA. rpaley1@swarthmore.edu
Berry
Katherine E
KE
Liu
Jane M
JM
Sanan
Toby T
TT
D000475:Alkenes / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D009942:Organometallic Compounds; D007501:Iron