Synthesis of 1,3-diamines through rhodium-catalyzed C-H insertion.
A grand opening: N-Boc-N-alkylsulfamides are effective substrates for the title transformation. Oxidative cyclization is highly chemoselective as well as being both stereospecific and diastereoselective. With the advent of new protocols that facilitate ring opening of the six-membered-ring heterocyclic products, access to differentially protected 1,3-diamines has been made possible (see scheme).
Kurokawa
Toshiki
T
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.
Kim
Mihyong
M
Du Bois
J
J
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D003959:Diamines; D002244:Carbon; D006859:Hydrogen; D012238:Rhodium