Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N, S-ketals. Issue 2 (11th January 2017)

• Record Type: Journal Article
• Authors: Unhale, Rajshekhar A.; Molleti, Nagaraju; Rana, Nirmal K.; Dhanasekaran, Sivasankaran; Bhandary, Subhrajyoti; Singh, Vinod K.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 2(2017)
• Page Start: 145
• Page End: 151
• Publication Date: 2017-01-11
• Subjects: Chiral phosphoric acid -- Organocatalysis -- N, S-Ketal -- Isoindolinone -- HIV-1 reverse transcriptase inhibitor; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.114
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Brønsted acid catalyzed enantioselective synthesis of N, S-ketals has been developed. The products are obtained in moderate to excellent yields and enantioselectivities. A known HIV-1 reverse transcriptase inhibitor has synthesized using this protocol. Abstract: The chiral Brønsted acid catalyzed enantioselective 1, 2-addition of thiols to in situ generated ketimines, derived from 3-hydroxyisoindolinones, has been studied. The protocol provides a variety of isoindolinone-derived N, S -ketals in up to 98% yield and up to 99% enantioselectivity. The products have been converted to a known non-nucleoside HIV-1 reverse transcriptase inhibitor and a 1, 3-thiazine derivative.