New Computational and Experimental Evidence for the Mechanism of the Sakurai Reaction

Author:

Bottoni Andrea1,Costa Anna Luisa1,Di Tommaso Donata1,Rossi Ivan1,Tagliavini Emilio1

Affiliation:

1. Contribution from the Dipartimento di Chimica “G. Ciamician”, Universita' di Bologna, Via Selmi 2, 40126 Bologna, Italy

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Reference26 articles.

1. Syntheses of γ,δ-unsaturated alcohols from allylsilanes and carbonyl compounds in the presence of titanium tetrachloride

2. Erythroselectivity in addition of γ-substituted allylsilanes to aldehydes in the presence of titanium chloride

3. Cyclic transition states have been proposed for the reactions of allylsilacyclobutanes (Matsumoto, K.; Oshima, K.; Utimoto, K.J. Org.Chem.1994,59, 7152) and allyltrifluorosilanes (Kobayashi, S.; Nishio, K.J.Org. Chem.1994,59, 6620). These transition structures have recently been determined with theoretical methods:  Fujimoto, H.; Omoto, K.; Sawada, Y.J.Am. Chem. Soc.1996,118, 1750−1755. Also the thermal or pressurized reaction of allylstannanes with aldehydes has been proposed to proceed through cyclic transition states:  Yamamoto, Y.; Maruyama, K.; Matsumoto, K.J. Chem. Soc., Chem. Commun.1983, 489. A theoretical investigation of the allylation with allyl tetrafluorosilicates has shown that this reaction involves a cyclyc transition structure:  Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J.Chem. Lett.1991, 387.

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