Sulfur-functionalized olefins for titanacycle formation: Tandem asymmetric cyclization and the pummerer reaction based on sulfoxides promoted by titanium(II)-to-titanium(IV) relay

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Abstract

Reusing the metal: Combination of the sulfoxide-based asymmetric enyne cyclization (Ti11 mediated) and the Pummerer reaction (Ti11 mediated) in tandem was effected by a reagent system consisting of a relay of titanium(II) to titanium(IV), which permits a one-pot synthesis of cyclic aldehydes in an optically active form (see scheme; To1 = p-tolyl).

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Narita, M., Urabe, H., & Sato, F. (2002). Sulfur-functionalized olefins for titanacycle formation: Tandem asymmetric cyclization and the pummerer reaction based on sulfoxides promoted by titanium(II)-to-titanium(IV) relay. Angewandte Chemie - International Edition, 41(19), 3671–3674. https://doi.org/10.1002/1521-3773(20021004)41:19<3671::AID-ANIE3671>3.0.CO;2-X

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