title: Synthesis of chiral γ-lactones by one-pot sequential enantioselective organocatalytic michael addition of boronic acids and diastereoselective intramolecular passerini reaction.
abstract: The synthesis of α,γ-substituted chiral γ-lactones was quickly achieved in a one pot sequential process. The procedure involves an enantioselective organocatalysed transfer of boronic acid to 5-hydroxyfuran-2(5H)-one, followed by an intramolecular diastereoselective Passerini-type reaction. The methodology was developed and optimized with N-Boc-indole-2-boronic acid giving access to α-indole-γ-substituted lactones in high yields and good diastereoisomeric and enantiomeric ratios. By applying the process to other boronic acids, the synthesis of structurally diversified α,γ-substituted chiral lactones was also achieved in good yields albeit with lower enantioselectivities.
authors.affiliation: Université de Reims Champagne-Ardenne , Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Maxence
authors.initials: M
authors.lastname: Bos
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Riguet