Abstract
Regio- and diastereoselective carbonyl allylations of 1-halobut-2-enes with tin(II) halides are described. Tin(II) bromide in a dichloromethane−water biphasic system is an effective reagent for unusual α-regioselective carbonyl allylation of 1-bromobut-2-ene to produce 1-substituted pent-3-en-1-ols. The addition of tetrabutylammonium bromide (TBABr) to the biphasic system produces 1-substituted 2-methylbut-3-en-1-ols via usual γ-addition which is opposite to the α-addition without TBABr. The γ-addition to aromatic aldehydes exhibits anti-diastereoselectivity, while that to aliphatic aldehydes is not diastereoselective. The allylation of benzaldehyde by 1-chlorobut-2-ene in 1,3-dimethylimidazolidin-2-one (DMI) does not occur with tin(II) chloride or bromide but does proceed with tin(II) iodide and exhibits γ-syn selectivity which is unusual for a Barbier-type carbonyl allylation. In the carbonyl allylation by 1-chlorobut-2-ene with any tin(II) halide, the addition of tetrabutylammonium iodide (TBAI) accele...
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