Enantioselective <i>anti</i>- and <i>syn</i>-(Borylmethyl)allylation of Aldehydes via Brønsted Acid Catalysis
Jiaming Liu, Ming Chen
Abstract
The enantioselective anti- and syn-(borylmethyl)allylation of aldehydes via phosphoric acid catalysis is reported. Both (E)- and (Z)-γ-borylmethyl allylboronate reagents were prepared via the Cu-catalyzed highly stereoselective protoboration of 1,3-dienylboronate. Chiral phosphoric acid-catalyzed aldehyde allylation with either the (E)- or (Z)-allylboron reagent provided 1,2-anti- or 1,2-syn-adducts in good yields with high enantioselectivities. The application to the synthesis of morinol D was accomplished.
Topics & Concepts
ChemistryEnantioselective synthesisPhosphoric acidCatalysisAldehydeReagentAdductBrønsted–Lowry acid–base theoryStereoselectivityOrganic chemistryCombinatorial chemistryOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods