Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions |
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Authors: | Fukuzawa Shin-ichi Yahara Yuusuke Kamiyama Akira Hara Masumi Kikuchi Satoshi |
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Institution: | Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan. fukuzawa@chem.chuo-u.ac.jp |
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Abstract: | reaction: see text] The pinacol coupling reaction of planar chiral ortho-oxazoline-substituted formylferrocene was smoothly mediated by SmI2 or Sm(OTf)3 to give the (R,R) isomer selectivity (up to 76% diastereomeric excess). The combination of Yb(OTf)3 and the (R,R)-ferrocenyl diol was revealed to be a good catalyst for the asymmetric Diels-Alder reaction of 3-acyloxazolidinone with cyclopentadiene, and the endo adduct was produced in up to 80% enantiomeric excess. |
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