Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols

Tomoya Miura; Yuuta Funakoshi; Masao Morimoto; Tsuneaki Biyajima; Masahiro Murakami

doi:10.1021/ja308285r

Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols

J Am Chem Soc. 2012 Oct 24;134(42):17440-3. doi: 10.1021/ja308285r. Epub 2012 Oct 15.

Authors

Tomoya Miura¹, Yuuta Funakoshi, Masao Morimoto, Tsuneaki Biyajima, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. tmiura@sbchem.kyoto-u.ac.jp

PMID: 23043352
DOI: 10.1021/ja308285r

Abstract

Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary α-imino rhodium(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Amines / chemical synthesis*
Amines / chemistry
Catalysis
Molecular Structure
Organometallic Compounds / chemistry*
Rhodium / chemistry*

Substances

Alcohols
Amines
Organometallic Compounds
Rhodium