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Paper | Special issue | Vol 52, No. 1, 2000, pp.195-201
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S8
Novel Palladium Chiral Phosphinooxazoline Complexes: Crystal Strucutre Studies and Application to Asymmetric Heck Reaction

Masamichi Ogasawara, Kazuhiro Yoshida, and Tamio Hayashi*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Abstract

The novel palladium(II) complexes coordinated with (S,S)- and (S,R)-2-[4-(isopropyl)oxazol-2-yl]-2'-diphenylphosphino-1,1'-binaphthyls (1a and 1b) were prepared and their structures were determined by X-Ray crystallography. The X-Ray single crystal structure studies reveal that the axially chiral binaphthyl skeletons are more strongly regulating the chiral environment around the palladium centers than the chiral carbon centers in the oxazoline moieties. The results from application of 1a and 1b to the asymmetric Heck reaction also supported this conclusion. The highest enantioselectivity (88% ee) was observed in (R)-2-phenyl-2,5-dihydrofuran which was obtained from 2,3-dihydrofuran and phenyl triflate catalyzed by Pd/1a.