Tetrahedron p. 3553 - 3562 (1996)
Update date:2022-09-26
Topics:
Bonini, Bianca F.
Masi, Enza
Masiero, Stefano
Mazzanti, Germana
Zani, Paolo
endo- and exo-trimethylsilyl-3-phenyl-2-thiabicyclo[2.2.1]hept-5-enes, the endo-trimethylsilyl-exo-S-oxide and their S,S-dioxide derivatives were protiodesilylated with fluoride ion. Stereoconvergent reactions were found, affording the endo-phenyl derivatives. These results can be rationalised with the hypothesis of a common carbanionic intermediate. In contrast, the desilylation of 3-endo-trimethylsilyl-3-exo-phenyl-2-thiabicyclo[2.2.1]heptane gave a mixture of endo- and exo-isomers, thus proving the involvement of the double bond in the control of the reaction stereoselectivity.
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