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

Zhilong Chen; Jianwei Sun

doi:10.1002/anie.201306801

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

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

Authors

Zhilong Chen¹, Jianwei Sun

Affiliation

¹ Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).

PMID: 24254193
DOI: 10.1002/anie.201306801

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols
Catalysis
Cyclization
Furans / chemical synthesis*
Furans / chemistry
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Stereoisomerism

Substances

Alcohols
Furans
Pyrans
tetrahydrofuran