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by orthogonal-tandem catalysis using the combination of HG-II
and CSA, which provided 2,6-cis-substituted tetrahydropyrans in
good yields with excellent diastereoselectivity. Our domino
reaction directly affords synthetically useful 2,6-cis-substituted
tetrahydropyrans from readily available starting materials and
obviates the need to isolate intermediary ζ-hydroxy α,β-unsatu-
rated carbonyl compounds.
Acknowledgements
We thank Mr Naoki Ichinokawa (Tohoku University) for his
helpful suggestions. This work was financially supported in part
by a Grant-in-Aid for Young Scientists (A) (No. 23681045) from
Japan Society for the Promotion of Science (JSPS) and by a
Grant-in-Aid for Scientific Research on Innovative Areas
“Organic Synthesis Based on Reaction Integration” (No.
22106504) from the Ministry of Education, Culture, Sports,
Science and Technology (MEXT), Japan.
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8112 | Org. Biomol. Chem., 2012, 10, 8108–8112
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