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

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 chemoselectivi...

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Veröffentlicht in:European journal of organic chemistry 2015-09, Vol.2015 (29), p.6413-6418
Hauptverfasser: Ramachary, Dhevalapally B., Shruthi, Kodambahalli S., Madhavachary, R.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500994