Au(I)- and Pt(II)-catalyzed cycloetherification of omega-hydroxy propargylic esters.
Depending on the nature of the metal catalyst, omega-hydroxy propargylic acetates choose between alternative cycloetherification manifolds to produce functionalized heterocycles in high yields. AuCl catalyzes the formation of oxacyclic enol acetates, whereas [Cl(2)Pt(CH(2)CH(2))]2 (Zeise's dimer) will induce a propargylic substitution via an unprecedented S(N)2'-type allenic substitution from within a chelated square planar cationic Pt(II) complex.
De Brabander
Jef K
JK
Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, TX 75390-9038, USA. jef.debrabander@utsouthwestern.edu
Liu
Bo
B
Qian
Mingxing
M
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004952:Esters; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D004952:Esters; D020005:Propanols; D010984:Platinum; D006046:Gold