A CONVENIENT 5-<i>exo-dig</i> CYCLIZATION ROUTE TO DIASTEREOMERICALLY PURE METHYL (2<i>S</i>)-2-(1-BENZYL-3-OXO-1,3-DIHYDRO-2<i>H</i>-ISOINDOL-2-YL)-3-METHYLBUTANOATE

Authors

  • Dnyaneshwar Nighot Department of Chemistry, Galgotias University, Plot No. 2, Sector 17-A, Yamuna Expressway, Greater Noida, Uttar Pradesh 201308, India
  • Arvind Kumar Jain Department of Chemistry, Galgotias University, Plot No. 2, Sector 17-A, Yamuna Expressway, Greater Noida, Uttar Pradesh 201308, India
  • Mandeep Singh Department of Chemistry, University of Delhi, New Delhi 110007, India
  • Varun Rawat Amity School of Applied Sciences, Amity University Haryana, Amity Education Valley, Gurugram, Haryana 122413, India

DOI:

https://doi.org/10.1007/5600

Keywords:

oxoisoindoline, cyclization, diastereoselectivity, enantioselectivity, Sonogashira coupling.

Abstract

A robust method toward the synthesis of diastereomerically pure methyl (2S)-2-(1-benzyl-3-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-methylbutanoate has been described. The key reactions in the synthesis are: HATU-mediated coupling, Pd-catalyzed Sonogashira coupling, base-mediated 5-exo-dig cyclization, and catalytic hydrogenation. The diastereomeric mixture is subjected to trituration with heptane to furnish both diastereomers in moderate yields. The relative stereochemistry was confirmed by the single crystal X-ray diffractometry. The key feature of the method is the simplicity of the diastereomeric separation.

Author Biography

Varun Rawat, Amity School of Applied Sciences, Amity University Haryana, Amity Education Valley, Gurugram, Haryana 122413, India

Assistant Professor

Amity School of Applied Science

Amity University Haryana

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Published

2020-11-05

Issue

Vol. 56 No. 10 (2020)

Section

Short Communications