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. 2013 Dec 16;52(51):13593-6.
doi: 10.1002/anie.201306801. Epub 2013 Nov 19.

Enantio- and diastereoselective assembly of tetrahydrofuran and tetrahydropyran skeletons with all-carbon-substituted quaternary stereocenters

Zhilong Chen  1 , Jianwei Sun
Affiliations

Enantio- and diastereoselective assembly of tetrahydrofuran and tetrahydropyran skeletons with all-carbon-substituted quaternary stereocenters

Zhilong Chen et al. Angew Chem Int Ed Engl. .

Abstract

Chiral phosphoric acids (HB*) catalyze the asymmetric desymmetrization of meso 1,3-diols through mono-transacetalization with a tethered acetal unit. This new strategy leads to the efficient assembly of tetrahydrofuran and tetrahydropyran skeletons bearing remote all-carbon-substituted quaternary stereocenters that are not straightforward to access by other methods.

Keywords: asymmetric catalysis; cyclization; organocatalysis; oxygen heterocycles.

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