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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 08.08.2014 by Andrei Malkov, Darren S. Lee, Mark Elsegood, Maciej Barlog, Pavel Kocovsky
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. 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 Journal

Volume

20

Issue

17

Pages

4901 - 4905

Citation

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-VCH

Version

AM (Accepted Manuscript)

Publication date

2014

Notes

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

0947-6539

eISSN

1521-3765

Language

en

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