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Palladium-catalyzed stereoselective intramolecular oxidative amidation of alkenes in the synthesis of 1,3- and 1,4-amino alcohols and 1,3-diamines
journal contribution
posted on 2014-08-08, 13:44 authored by Andrei MalkovAndrei Malkov, Darren S. Lee, Mark ElsegoodMark Elsegood, Maciej Barlog, Pavel KocovskyAn efficient and practical Pd-catalyzed intramolecular oxidative allylic amidation provides facile access to derivatives of 1,3- and 1,4-amino alcohols and 1,3-diamines. The method operates under mild reaction conditions (RT) with molecular oxygen (1 atm) as the sole reoxidant of Pd. Excellent diastereoselectivities were attained with substrates bearing a secondary stereogenic center Nitrogen in, hydrogen out: An efficient and practical Pd-catalyzed intramolecular oxidative allylic amidation provides facile access to derivatives of 1,3- and 1,4-amino alcohols and 1,3-diamines (see scheme). The method operates under mild reaction conditions (RT) with molecular oxygen (1 atm) as the sole reoxidant of Pd. Excellent diastereoselectivities were attained with substrates bearing a secondary stereogenic center.
History
School
- Science
Department
- Chemistry
Published in
Chemistry - A European JournalVolume
20Issue
17Pages
4901 - 4905Citation
MALKOV, A.V. ... et al., 2014. Palladium-catalyzed stereoselective intramolecular oxidative amidation of alkenes in the synthesis of 1,3- and 1,4-amino alcohols and 1,3-diamines. Chemistry : a European Journal, 20 (17), pp. 4901-4905.Publisher
© Wiley-VCHVersion
- AM (Accepted Manuscript)
Publication date
2014Notes
This is the peer reviewed version of the following article: MALKOV, A.V. ... et al., 2014. Palladium-catalyzed stereoselective intramolecular oxidative amidation of alkenes in the synthesis of 1,3- and 1,4-amino alcohols and 1,3-diamines. Chemistry : a European Journal, 20 (17), pp. 4901-4905, which has been published in final form at: http://dx.doi.org/10.1002/chem.201400123.ISSN
0947-6539eISSN
1521-3765Publisher version
Language
- en