Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N,S-ketals

doi:10.1016/j.tetlet.2016.11.114

Tetrahedron Letters

Volume 58, Issue 2, 11 January 2017, Pages 145-151

https://doi.org/10.1016/j.tetlet.2016.11.114 Get rights and content

Highlights

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Brønsted acid catalyzed enantioselective synthesis of N,S-ketals has been developed.
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The products are obtained in moderate to excellent yields and enantioselectivities.
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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.

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Acknowledgments

Financial support through the J.C. Bose fellowship (DST, India) and SERB, DST (EMR/2014/ 001165), India for research grant are gratefully acknowledged. R.A.U. and S.B. thank CSIR, New Delhi for SPM and SRF fellowship, respectively. N.M. thanks IISER Bhopal for a post-doc fellowship. N.K.R. thanks DST for a fellowship and research grant through the INSPIRE Faculty award. We gratefully acknowledge Dr. Jhasaketan Sahu, IIT Kanpur and Dr. Deepak Chopra from IISER Bhopal for assistance with X-ray

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Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N,S-ketals

Highlights

Abstract

Graphical abstract

Section snippets

Acknowledgments

Angew Chem Int Ed

Org Lett

Org Lett

Org Lett

Adv Synth Catal

Org Lett

Chem Commun

The Chemistry of Optically Active Sulfur Compounds

Beilstein J Org Chem

Chem Rev

J Am Chem Soc

J Am Chem Soc

Angew Chem Int Ed

J Am Chem Soc

Chem Commun

Adv Synth Catal

Angew Chem Int Ed

J Org Chem

J Am Chem Soc

J Mol Catal A

Chem Sci

Org Lett

Org Lett

Tetrahedron Asymmetry

Org Lett

J Med Chem

J Heterocycl Chem