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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Mahato, CK; Mukherjee, S; Kundu, M; Vallapure, VP; Pramanik, A

Published Date

  • April 2, 2021

Published In

Volume / Issue

  • 86 / 7

Start / End Page

  • 5213 - 5226

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/acs.joc.1c00124

Citation Source

  • Scopus