Titanium(IV)-Promoted Mukaiyama Aldol−Prins Cyclizations
2003; American Chemical Society; Volume: 5; Issue: 17 Linguagem: Inglês
10.1021/ol035303n
ISSN1523-7060
AutoresBrian D. Patterson, Shinji Marumoto, Scott D. Rychnovsky,
Tópico(s)Marine Sponges and Natural Products
ResumoA new version of the Mukaiyama aldol−Prins (MAP) cyclization has been developed. Unsaturated enol ethers such as 3 were found to couple with aldehydes in the presence of TiBr4 to give 4-bromotetrahydropyran products. This cascade reaction sequence leads to the formation of two new carbon−carbon bonds, a ring, and three new stereogenic centers. We expect this reaction to be a powerful new tool in synthesis.
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