Alpha-methylene-beta-amino ketone derivatives from beta-ketoallylsilanes

M Antonietta Loreto; Antonella Migliorini; P Antonio Tardella

doi:10.1021/jo052330d

Alpha-methylene-beta-amino ketone derivatives from beta-ketoallylsilanes

J Org Chem. 2006 Mar 3;71(5):2163-6. doi: 10.1021/jo052330d.

Authors

M Antonietta Loreto¹, Antonella Migliorini, P Antonio Tardella

Affiliation

¹ Dipartimento di Chimica, Università La Sapienza, Piazzale Aldo Moro 5, 00185 Rome, Italy. mariaantonietta.loreto@uniroma1.it

PMID: 16497010
DOI: 10.1021/jo052330d

Abstract

Beta-Ketoallylsilanes are synthesized by the Horner-Emmons reaction starting from novel silylated ketophosphonates and various aldehydes. The reactions of beta-ketoallylsilanes with NsONHCO2Et and CaO produce alpha-methylene-N-(ethoxycarbonyl)-beta-amino ketones through the ring opening of the intermediate aziridine, which is favored by the presence of the trimethylsilyl group. With chiral beta-ketoallylsilanes we obtained a stereoselective amination reaction with a 90% diastereomeric excess. alpha-Methylene-N-(ethoxycarbonyl)-beta-amino ketones are isolated in 39-60% yields and characterized.

Publication types

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

MeSH terms

Alkenes / chemistry*
Ketones / chemical synthesis*
Silanes / chemistry*

Substances

Alkenes
Ketones
Silanes
allylsilane