Work

Stereoselective Synthesis of Substituted Oxocene Cores by Lewis Acid Promoted Cyclization

Year: 2016

Type: article

Abstract: Substituted oxocene derivatives have been synthesized by Lewis acid catalyzed reactions of ε-hydroxyalkene and substituted aromatic aldehydes. The Cu(OTf)2-bis-phosphine catalyzed reaction typically provides substituted dihydropyran derivatives through an olefin migration followed by a Prins cyclization. The corresponding reaction catalyzed by TMSOTf or BF3·OEt2 provided eight-membered cyclic ethers (oxocenes), selectively. This methodology provides convenient access to a variety of 2,4,8-trisubstituted oxocenes in good yields and excellent diastereoselectivities.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5b03411

Authors: Arun K. Ghosh, Anthony J. Tomaine, Kelsey E. Cantwell

Institution: Purdue University West Lafayette

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Cancer Institute, National Institute of General Medical Sciences

Awards: G5103706978, Cancer Center Support Grant, DESIGN AND SYNTHESIS OF NONPEPTIDE PROTEASE INHIBITORS, Design & Synthesis of Nonpeptide Protease Inhibitors