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Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts

Publication ,  Journal Article
Mahato, CK; Mukherjee, S; Kundu, M; Vallapure, VP; Pramanik, A
Published in: Journal of Organic Chemistry
April 2, 2021

Organic transformations exclusively in water as an environmentally friendly and safe medium have drawn significant interest in the recent years. Moreover, transition metal-free synthesis of enantiopure molecules in water will have a great deal of attention as the system will mimic the natural enzymatic reactions. In this work, a new set of proline-derived hydrophobic organocatalysts have been synthesized and utilized for asymmetric Michael reactions in water as the sole reaction medium. Among the various catalysts screened, the catalyst 1 is indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to >99.9%) resulting in high chemical yields (up to 95%) in a very short reaction time (1 h) at room temperature. This methodology provides a robust, green, and convenient protocol and can thus be an important addition to the arsenal of the asymmetric Michael addition reaction. Upon successful implementation, the present strategy also led to the formation of an optically active octahydroindole, the key component found in many natural products.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

April 2, 2021

Volume

86

Issue

7

Start / End Page

5213 / 5226

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Mahato, C. K., Mukherjee, S., Kundu, M., Vallapure, V. P., & Pramanik, A. (2021). Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts. Journal of Organic Chemistry, 86(7), 5213–5226. https://doi.org/10.1021/acs.joc.1c00124
Mahato, C. K., S. Mukherjee, M. Kundu, V. P. Vallapure, and A. Pramanik. “Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts.” Journal of Organic Chemistry 86, no. 7 (April 2, 2021): 5213–26. https://doi.org/10.1021/acs.joc.1c00124.
Mahato CK, Mukherjee S, Kundu M, Vallapure VP, Pramanik A. Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts. Journal of Organic Chemistry. 2021 Apr 2;86(7):5213–26.
Mahato, C. K., et al. “Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts.” Journal of Organic Chemistry, vol. 86, no. 7, Apr. 2021, pp. 5213–26. Scopus, doi:10.1021/acs.joc.1c00124.
Mahato CK, Mukherjee S, Kundu M, Vallapure VP, Pramanik A. Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts. Journal of Organic Chemistry. 2021 Apr 2;86(7):5213–5226.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

April 2, 2021

Volume

86

Issue

7

Start / End Page

5213 / 5226

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry