Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines.
This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives.
Maji
Modhu Sudan
MS
NRW Graduate School of Chemistry and Fachbereich Chemie, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Münster, Germany.
Fröhlich
Roland
R
Studer
Armido
A
D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D053138:Cyclohexenes; D007097:Imines; D009942:Organometallic Compounds; D008274:Magnesium; D015032:Zinc