Cyclohexane-1,2-diamines: Efficient Catalysts for the Enantioselective Conjugate Addition of Ketones to Nitro Olefins

Rasappan, Ramesh and Reiser, Oliver (2009) Cyclohexane-1,2-diamines: Efficient Catalysts for the Enantioselective Conjugate Addition of Ketones to Nitro Olefins. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (9). pp. 1305-1308. ISSN 1434-193X, 1099-0690

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Abstract

Simple monosulfonated cyclobexane-1,2-diamines are highly enantioselective organocatalysts for the conjugate addition of ketones to nitro olefins. By focusing on aromatic ketones as the most challenging substrates, selectivities of up to 98 % ee can be achieved for the title reaction. Moreover, a three-component process between the primary amine catalyst, the nitroalkene, and the ketone, which results in the irreversible formation of pyrrols has been recognized as a reaction pathway for catalyst deactivation. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Item Type: Article
Uncontrolled Keywords: ASYMMETRIC MICHAEL ADDITION; BIFUNCTIONAL ORGANOCATALYSTS; PYRROLIDINE-THIOUREA; NITROOLEFINS; NITROSTYRENE; NITROALKENES; ALDEHYDES; Organocatalysis; Enantioselectivity; Conjugate addition; Amines
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 22 Sep 2020 10:13
Last Modified: 22 Sep 2020 10:13
URI: https://pred.uni-regensburg.de/id/eprint/29348

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