ChemInform Abstract: Control of Five Contiguous Stereogenic Centers in an Organocatalytic Kinetic Resolution via Michael/Acetalization Sequence: Synthesis of Fully Substituted Tetrahydropyranols.

Abstract

Tetrahydropyranols. -The conversion of aldehydes with a range of aryl substituted secondary nitroallylic alcohols in the presence of a chiral prolinol derivative furnishes the title products with excellent stereoselectivities. The recovered, less reactive nitroallylic alcohol ((S)-Ia) can be further transformed via diastereoselective reduction of its double bond en route to enantioenriched 3-amino-2-hydroxy-phenylbutyric acids which are precursors of numerous biologically active skeletons including aminopeptidase and HIV-1 protease inhibitors. -(GURUBRAHAMAM, R.; CHENG, Y.-S.; CHEN*, K.; Org. Lett. 17 (2015) 3, 430-433, http://dx.