Ureidoallylation of double bonds

✍ Scribed by Robert R. Webb II; Samuel Denishefsky

• Book ID: 104217105
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 186 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81655-x

✦ Synopsis

Intramolecular ureidoselenenylation of double bonds followed by allylative de-selenenylation accomplishes a net ureidoallylation. In furtherance of some new departures in the synthesis of alkaloids, methodology directed toward the formalism J, + ,$ was investigated. The sequence of intramolecular addition of a nitrogen-based group to an unactivated double bond followed by attachment of a functionalized carbon array would find broad application. 192 The attainment of this scheme for the case of R' = ally1 is described below. Intramolecular ureidoselenenylation of the general system 2, using the Nicolaou reagent N-phenylselenophthalimide (N-PSP),3 establishes the carbon-nitrogen bond. An ally1 group is introduced by the action of $, with tri-n-butylallylstannane with initiation by azobisisobutyronitrile (AIBN). Such a protocol was developed by Keck and co-workers4 for the replacement of carbon bound halogens by ally1 functions and used in the Utah synthesis of perhydrohistrionico.