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Synlett 2000; 2000(9): 1245-1248
DOI: 10.1055/s-2000-7130
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Chiral SEM Ether-Tin Tetrachloride as an Enantioselective Hydroxymethylating Reagent for Trisubstituted Alkenes

Kazuaki Ishihara* , Hiroko Nakamura, Hisashi Yamamoto
  • *Research Center for Advanced Waste and Emission Management, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan
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Publication Date:
31 December 2000 (online)

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A new and efficient method for the enantioselective Prins reaction (acetal-ene reaction) of trisubstituted alkenes to give optically active homoallylic ethers is described. (R)-BINOL-(SEM)2 serves as a synthetic equivalent of formaldehyde, and the Prins reaction occurs even at - 97 °C in the presence of thin tetrachloride. The 2-(trimethylsilyl)ethyl group of the resulting homoallylic ethers was easily removed by treatment with hydrogen fluoride-pyridine.

enantioselective Prins reactions - homoallylic alcohols - tin tetrachloride - SEM - hydrogen fluoride

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