Stereoselective synthesis of contiguous THF-THF and THF-THP units via Pd-II-catalyzed tandem reaction with 1,3-chirality transfer

作者：Kawai Nobuyuki^*; Fujikura Yuhei; Takita Jun; Uenishi Jun'ichi

来源：Tetrahedron, 2013, 69(51): 11017-11024.

DOI：10.1016/j.tet.2013.09.067

• Contiguous THF-THF and THF-THP
• Pd(II)-catalyst
• Tandem reaction
• 1,3-Chirality transfer
• Oxygen-fused THP-THP rings

The Pd-II-catalyzed tandem cyclization of chiral allylic alcohols possessing an internal epoxide and a terminal alcohol provided a contiguous THF-THP and THF-THP ring units stereospecifically. The cyclizations take place via a 5-exo-tet-5-exo-trig mode, however, the cyclization of methyl substituted epoxy diols proceeded via 6-endo-tet-6-exo-trig fashion in a part to construct the oxygen-fused THP-THP ring. The different reaction rates of precursors, which are different stereochemistry at allylic alcohol have been elucidated.

• 出版日期2013-12-23