title: Chiral Brønsted acid-catalysed enantioselective synthesis of isoindolinone-derived N(acyl),S-acetals.
abstract: The first organocatalytic asymmetric addition of thiols to N-acyl ketimines, which are generated in situ from 3-hydroxy isoindolinones, is described. The reaction proceeds smoothly with a broad range of ketimines and thiols using a chiral Brønsted acid catalyst to afford N(acyl),S-acetals comprising a tetrasubstituted stereocenter in high yields and enantioselectivities (up to 98.5 : 1.5 e.r.). The usefulness of the developed protocol is demonstrated in the synthesis of a known HIV-1 reverse transcriptase inhibitor.
authors.affiliation: Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia. matija.gredicak@irb.hr.
authors.forename: Josipa
authors.initials: J
authors.lastname: Suć
authors.affiliation: Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia. matija.gredicak@irb.hr.
authors.forename: Irena
authors.initials: I
authors.lastname: Dokli
authors.affiliation: Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia. matija.gredicak@irb.hr.
authors.forename: Matija
authors.initials: M
authors.lastname: Gredičak