2,2-Difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions.
N-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-L-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Luke D
LD
Elliott
Joe W
JW
Wrigglesworth
Brian
B
Cox
Guy C
GC
Lloyd-Jones
Kevin I
KI
Booker-Milburn
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D048289:Imidazolidines; D010080:Oxazoles; C064210:oxazolidine; D010165:Palladium