Tsuji-Trost reaction intramolecular addition

While the reaction of aliphatic alcohols can be problematic, there are several examples reported in the synthesis of complex molecular targets. For example, the use of Tsuji-Trost reaction in the synthesis of cis-2,5-disubstituted tetrahydrofiirans was reported by Williams and co-workers. They used a soft oxygen nucleophile in an intramolecular reaction to prepare the C7-C22 core of amphidinolide K 45. It was found the addition of MesSnCl was necessary to both suppress acyl migration and ensure the oxygen was strongly nucleophilic. 

Furthermore, following an analogous methodology, combining the Morita-Baylis-Hillman reaction and the Trost-Tsuji reaction, Krische and co-workers have obtained allyl-substituted cyclopentenones 94 [84], Reaction was initiated by Michael addition of tributyl phosphine to an enone moiety 92, generating a latent enolate 93 which reacts intramolecularly with a jr-allylPd complex as the electrophile partner. A final -elimination step of trib-utylphosphine, favored by the presence of the methoxide ion, delivered the substituted cyclopentenones 94 (Scheme 36). 

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