cheminform abstract: stereoselective synthesis of silacyclohexanols by silicon tethered type ii ene...

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2001 organo-silicon compounds organo-silicon compounds S 0060 09 - 151 Stereoselective Synthesis of Silacyclohexanols by Silicon Tethered Type II Ene Cyclization. The preparation of vinyl silane precursors like (I), (III), (IX) and (XIV) for intramolecular ene reactions is described. Their synthesis is achieved either by sequential organometallic substitution of appropriate silyl halides or by ring opening of oxasilacyclopentanes with propenyllithium. Treatment of this ene precursors with methylaluminum dichloride gives the corresponding silacyclohexanols in good yields and with high stereoselectivity. — (ROBERTSON, JEREMY; O’CONNOR, GARRY; SARDHARWALA, TSARINA; MIDDLETON, DONALD S.; Tetrahedron 56 (2000) 42, 8309-8320; Dyson Perrins Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3QY, UK; EN) 1

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Page 1: ChemInform Abstract: Stereoselective Synthesis of Silacyclohexanols by Silicon Tethered Type II Ene Cyclization

2001 organo-silicon compounds

organo-silicon compoundsS 0060

09 - 151Stereoselective Synthesis of Silacyclohexanols by Silicon TetheredType II Ene Cyclization. — The preparation of vinyl silane precursorslike (I), (III), (IX) and (XIV) for intramolecular ene reactions is described.Their synthesis is achieved either by sequential organometallic substitutionof appropriate silyl halides or by ring opening of oxasilacyclopentanes withpropenyllithium. Treatment of this ene precursors with methylaluminumdichloride gives the corresponding silacyclohexanols in good yields and withhigh stereoselectivity. — (ROBERTSON, JEREMY; O’CONNOR, GARRY;SARDHARWALA, TSARINA; MIDDLETON, DONALD S.; Tetrahedron 56(2000) 42, 8309-8320; Dyson Perrins Lab., Dep. Chem., Univ. Oxford, OxfordOX1 3QY, UK; EN)

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