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Synfacts 2015; 11(5): 0513
DOI: 10.1055/s-0034-1380598
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric [4+2] Cycloaddition of Isochromene Acetals with Boronates

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Luan Y, Barbato KS, Moquist PN, Kodama T, Schaus SE * Boston University, USA
Enantioselective Synthesis of 1,2-Dihydronaphthalene-1-carbaldehydes by Addition of Boronates to Isochromene Acetals Catalyzed by Tartaric Acid.

J. Am. Chem. Soc. 2015;
137: 3233-3236
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Publication History

Publication Date:
17 April 2015 (online)

 
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Key words

[4+2] cycloaddition - tartaric acid - holmium

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).


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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.


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