Sakurai Reaction (Hosomi-Sakurai Reaction)

A. Hosomi, H. Sakurai, Tetrahedron Letters 1976, 1295; A. Hosomi et al., Chem. Letters 1976, 941.

Lewis acid-promoted nucleophilic addition of allylic silanes to carbon electrophiles accompanied by regiospecific transposition of the allylic moiety:



Synthetic applications: I. E. Markó, D. J. Bayston, Tetrahedron Letters 34, 6595 (1993); H. Hioki et al., ibid. 6131. [TiCp₂(OSO₂CF₃)₂] as catalyst: T. K. Hollis et al., ibid. 4309. Reviews: I. Fleming et al., Org. React. 37, 57-575 (1989); Y. Yamamoto, N. Sasaki, “The Stereochemistry of the Sakurai Reaction” in Stereochemistry of Organometallic and Inorganic Compounds vol. 3, I. Bernal, Ed. (Elsevier, New York, 1989) pp 363-437; I. Fleming, Comp. Org. Syn. 2, 563-593 (1991).