Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans

作者：McDonald Frank E^*; Ishida Kento; Hurtak Jessica A

来源：Tetrahedron, 2013, 69(36): 7746-7758.

DOI：10.1016/j.tet.2013.04.138

• Alcohol
• Alkene
• Alkyne
• Cyclic ether
• Diastereoselectivity
• Oxacyclization

Stereoinduction from the allylic hydroxyl group of 1,4-dihydroxy-5-alkenes has been systematically explored with various alkene substitution patterns and electrophilic reagents. For formation of erythro-diastereomers of 2-substituted 3-hydroxytetrahydropyrans, mercuric trifluoroacetate-promoted cyclizations of cis- and (Z)-alkenyldiols generally give the highest diastereoselectivities. For the corresponding 1,4-dihydroxy-5-alkyne, mercuric triflate-catalyzed cyclization followed by triethylsilane reduction affords an alternative route to the euthro-diastereomer.

• 出版日期2013-9-9