title: A general process for the haloamidation of olefins. Scope and mechanism.
abstract: A methodology is described for the addition of a bromine atom and an amide nitrogen in a trans sense to an olefinic double bond. The process, which is illustrated by numerous examples, involves the use of an N-bromoamide and a Lewis acid as a source of Br+ which reacts with the olefin. The amide group is derived from a nitrile and a water molecule which serve as nucleophiles for the overall three-component reaction. The bromoamidation is general for a broad range of olefins and nitriles. This reaction pathway provides access not only to vicinal bromoamides but also to N-acyl aziridines and oxazolines. From these, many types of amines and amino alcohols can be prepared. Examples are provided which delineate diastereo- and regioselectivity preferences. An analogous chloroamidation reaction is also described.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: Ying-Yeung
authors.initials: YY
authors.lastname: Yeung
authors.forename: Xuri
authors.initials: X
authors.lastname: Gao
authors.forename: E J
authors.initials: EJ
authors.lastname: Corey