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Issue 40, 2014
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Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

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Abstract

Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtained in higher yields (up to 99%) and excellent stereoselectivities (up to >99/1 dr and 99% ee). Transition state models have been proposed to account for the high enantio- and diastereoselectivity of these Michael addition reactions and also the energetics have been investigated using density functional methods. These results support the preferential formation of syn-products by the approach of trans-β-nitrostyrene through the re-face of anti-enamine.

Graphical abstract: Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

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Publication details

The article was received on 16 Jun 2014, accepted on 11 Aug 2014 and first published on 13 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01223B
Citation: Org. Biomol. Chem., 2014,12, 8008-8018
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    Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

    A. Kamal, M. Sathish, V. Srinivasulu, J. Chetna, K. Chandra Shekar, S. Nekkanti, Y. Tangella and N. Shankaraiah, Org. Biomol. Chem., 2014, 12, 8008
    DOI: 10.1039/C4OB01223B

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