166772-07-2Relevant articles and documents
Preparation and some reactions of neophyltin anions
Podesta, J. C.,Chopa, A. B.,Giagante, N. N.,Zuniga, A. E.
, p. 5 - 10 (2007/10/02)
A study on the preparation on the trineophyltin and mixed methylneophyltin anions and subsequent reactions of these anions is reported.It was found that whereas mixed hydrides MenNph3-nSnH (n=1,2) react with NaH in DMSO to give the corresponding organotin sodium anions (60-70percent yield), trineophyltin hydride reacts with NaH to give hexaneophylditin as the only product (32 percent).The reaction of tin halides MenNph3-nX (X = Cl, Br; n = 0, 1, 2) with lithium in THF yields the corresponding organotinlithium anions (70 percent).The tin anions were reacted with various alkylhalides.The 1,4 addition of trineophyltinlithium (10) to α,β-unsaturated enones followed by the reaction of the intermediate carbanions with methyl iodide, leads with benzylideneacetone to a mixture of the corresponding threo (34 percent) and erythro (25 percent) diastereoisomers.Under the same reaction conditions, the addition of 10 to chalcone proceeded with complete stereoselectivity to give the diastereoisomer threo (60 percent) as the only product.Full 1H and 13C NMR data of the new organotins are given. Keywords: Tin; Stereoselective synthesis
