Hisashi Yamamoto, M. Sai
May 1, 2015
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Abstract
Significance: The authors present the tartaric acid catalyzed asymmetric [4+2] cycloaddition of isochromene acetals with vinylboronates. A series of 1,2-dihydronaphthalene-1-carbaldehydes were prepared with excellent yields (up to 91%), diastereo(dr up to >99:1), and enantioselectivities (er up to 98.5:1.5). Comment: This method provides a facile access to chiral dihydronaphthalene building blocks that can be used to make important natural products and biological active compounds. Tartaric acid in combination with Ho(OTf)3 is highly effective for the reaction. Selected examples: O