Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis.
The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Malhotra
Sushant
S
Olson
David E
DE
Maruniak
Autumn
A
Du Bois
J
J
D000498:Allyl Compounds / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003959:Diamines / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000498:Allyl Compounds; D003959:Diamines; D008024:Ligands; D011073:Polyamines; D012997:Solvents; D010165:Palladium; D012238:Rhodium; D009584:Nitrogen; D010100:Oxygen