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Synlett 2001; 2001(Special Issue): 0989-0990
DOI: 10.1055/s-2001-14642
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A New Synthetic Route to (S)-Chroman Aldehyde, a Key Chiral Precursor of Vitamin E

Hisashi Mikoshiba* , Koichi Mikami, Takeshi Nakai
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan; Fax + 81-(0)3-5734-2885; E-mail: takeshi@o.cc.titech.ac.jp
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Publication History

Publication Date:
31 December 2001 (online)

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A highly stereocontrolled synthetic route to (S)-chroman aldehyde has been developed which starts with trimethyl-p-hydroquinone and (R)-glyceraldehyde acetonide and employs as key steps the Michael addition of the aromatic copper species onto the (R)-4-acryloyl-1,3-dioxolane followed by the highly diastereoselective methylation of the resulting ketone adduct.

chroman aldehyde - diastereoselectivity - glycerketone - Michael addition - vitamin E

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