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In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)methyl]propene (1) reacts with sequentially added aldehydes to provide cis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon aldehyde (R1CHO) allylation in aqueous media, acts as a promoter for the silyl-Prins reaction with the second equivalent of added aldehyde (R2CHO). The preparation of cyclohexenyl-fused pyrans via this one-pot, three-component coupling process is presented, as is a short formal synthesis of (+/-)-centrolobine.
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Pham et al. (2007) studied this question.
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