title: Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines.
abstract: Diverse N,N,O-trisubstituted hydroxylamines, an under-represented group in compound collections, are readily prepared by partial reduction of N-acyloxy secondary amines with diisobutylaluminum hydride followed by acetylation and reduction of the so-formed O-acyl-N,N-disubstituted hydroxylamines with triethylsilane and boron trifluoride etherate. Use of carbon nucleophiles in the last step, including allyltributylstannane, silyl enol ethers, and 2-methylfuran, gives N,N,O-trisubstituted hydroxylamines with branching α- to the O-substituent. N,N-Disubstiuted hydroxylamines are conveniently prepared by reaction of secondary amines with dibenzoyl peroxide followed by diisobutylaluminum hydride reduction.
authors.affiliation: Department of Chemistry, Wayne State University , Detroit, Michigan 48202, United States.
authors.forename: Sandeep
authors.initials: S
authors.lastname: Dhanju
authors.affiliation: Department of Chemistry, Wayne State University , Detroit, Michigan 48202, United States.
authors.forename: David
authors.initials: D
authors.lastname: Crich