A tandem Prins spirocyclization for the stereoselective synthesis of tetrahydrospiro[chroman-2, 4′-pyran] derivatives. Issue 12 (26th February 2016)

• Record Type: Journal Article
• Authors: Subba Reddy, B. V.; Hanuman Reddy, V.; Medaboina, Durgaprasad; Sridhar, B.; Rami Reddy, Y. V.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 12(2016)
• Page Start: 3234
• Page End: 3237
• Publication Date: 2016-02-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02639c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel cascade process has been developed for the synthesis of tetrahydrospiro[chroman-2, 4′-pyran] derivatives by condensation of aldehydes with 2-(5-hydroxy-3-methylenepentyl)phenols using BF3 ·OEt2 under mild reaction conditions. Abstract : A novel cascade strategy has been developed for the synthesis of tetrahydrospiro[chroman-2, 4′-pyran] derivatives by condensation of aldehydes with 2-(5-hydroxy-3-methylenepentyl)phenol. The reaction proceeds smoothly in the presence of BF3 ·OEt2 under mild conditions in a highly stereoselective manner leading to a single diastereomer. This approach is simple and convenient for the synthesis of pharmacologically relevant spirochroman scaffolds.