A Modularly Designed Supramolecular Organocatalyst as an Effective Stimulant for the Highly Asymmetric Michael Addition of Ketones to Nitro Olefins

Dhevalapally B. Ramachary*, Kodambahalli S. Shruthi, R. Madhavachary

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

11 Citations (Scopus)

Abstract

The asymmetric modularly designed supramolecular organocatalytic nitro olefin-ketone Michael addition of a variety of functionally rich nitro olefins with ketones was explored. The modularly designed supramolecular organocatalytic Michael reaction is characterized by a high rate, high chemoselectivity, high diastereoselectivity, high enantioselectivity, mild reaction conditions, readily available substrates/catalysts with simple operations, and excellent yields with a broad spectrum of functionally rich substrates. This method constitutes an alternative to previously known organocatalytic Michael reactions. We demonstrate the power of a supramolecular organocatalyst as an excellent stimulant for the highly reactive Michael addition of various ketones with functionally rich (E)-nitro olefins under ambient conditions to furnish enantiomerically pure carbamates and tetrahydroacridines; Cbz = benzyloxycarbonyl.

Original languageEnglish
Pages (from-to)6413-6418
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number29
DOIs
Publication statusPublished - 1 Sep 2015

Keywords

  • Asymmetric catalysis
  • Michael addition
  • Nitrogen heterocycles
  • Organocatalysis
  • Supramolecular chemistry

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