Bulletin of the Chemical Society of Japan p. 465 - 470 (1999)
Update date:2022-08-11
Topics:
Moriuchi-Kawakami, Takayo
Matsuda, Haruo
Shibata, Ikuya
Miyatake, Masato
Suwa, Toshihiro
Baba, Akio
We have found that halogen-exchange occurs effectively between Sn-F and Li-X (X = I, Br, Cl) in tin hydride reagents. This fact induced a complete change in the regiochemistry in the reductions of α,β-unsaturated ketones 1 with Bu2SnH2-Bu2SnF2 (Reagent A): the use of Reagent A in combination with HMPA performed 1,2-reductions, while the addition of LiI to Reagent A achieved 1,4-reductions. It was demonstrated that the regioselectivity of organotin hydrides greatly depends on the properties of the halogen substituents attached to tin atoms.
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