Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates.

Lakhdar, Sami; Baidya, Mahiuddin and Mayr, Herbert (2012): Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates. In: Chemical Communications, Vol. 48, No. 37: pp. 4504-4506

Abstract

The imidazoles 1a–g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = sN(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals.

• Item Type: Journal article
• Form of publication: Publisher's Version
• Faculties: Chemistry and Pharmacy
• Subjects: 500 Science > 540 Chemistry
• Alliance/National Licence: This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.
• Language: English