The Evans Aldol–Prins cyclization: a general and stereoselective method for the synthesis of 2, 3, 4, 5, 6-pentasubstituted tetrahydropyrans. Issue 16 (1st February 2016)

• Record Type: Journal Article
• Authors: Álvarez-Méndez, Sergio J.; García, Celina; Martín, Víctor S.
• Is Part Of: Chemical communications. Volume 52:Issue 16(2016)
• Page Start: 3380
• Page End: 3383
• Publication Date: 2016-02-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc00160b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A method for the synthesis of 2, 3, 4, 5, 6-pentasubstituted THPs with good yields and diastereoselectivities through an Evans Aldol–Prins strategy is described. Abstract : A general and stereoselective method to synthesize 2, 3, 4, 5, 6-pentasubstituted tetrahydropyrans in three steps starting from three different aldehydes is described. Key substrates β, γ-unsaturated N -acyloxazolidin-2-ones were subjected to an "Evans Aldol–Prins" protocol to generate five σ-bonds and five stereocenters in only a one-pot process with yields up to 60% and excellent stereoselectivities.