Chemoselective Reductive Alkylation of Ammonia with Carbonyl Compounds: Synthesis of Primary and Symmetrical Secondary Amines

Author(s)

Bruhaspathy Miriyala, University of Mississippi
Sukanta Bhattacharyya, Vijoygarh College
John S. Williamson, University of DaytonFollow

Document Type

Article

Publication Date

2-2004

Publication Source

Tetrahedron

Abstract

An efficient, general procedure for highly chemoselective reductive mono-alkylation of ammonia with ketones is reported. Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ sodium borohydride reduction, and a straightforward workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes, on the other hand, afforded the corresponding symmetrical secondary amines selectively.

Inclusive pages

1463–1471

ISBN/ISSN

0040-4020

Comments

Permission documentation is on file.

Copyright

Copyright © 2003, Elsevier

Publisher

Elsevier

Volume

60

Issue

7

Peer Reviewed

yes

eCommons Citation

Miriyala, Bruhaspathy; Bhattacharyya, Sukanta; and Williamson, John S., "Chemoselective Reductive Alkylation of Ammonia with Carbonyl Compounds: Synthesis of Primary and Symmetrical Secondary Amines" (2004). Office for Research Publications and Presentations. 23.
https://ecommons.udayton.edu/ofr_pub/23