Retention of configuration on the oxidative addition of P-H bond to platinum (0) complexes: the first straightforward synthesis of enantiomerically pure P-chiral alkenylphosphinates via palladium-catalyzed stereospecific hydrophosphinylation of alkynes.
The oxidative addition of pure (R(P))-menthyl phenylphosphinate 1 to a platinum (0) complex proceeds readily with retention of configuration at the chiral phosphorus center which was unambiguously confirmed by an X-ray analysis. In the presence of a catalytic amount of palladium, the hydrophosphinylation of a variety of alkynes with 1 also takes place stereospecifically, with retention of configuration, affording high yields of the corresponding vinylphosphinates bearing a single chirality at phosphorus.
Han
Li-Biao
LB
National Institute of Advanced Industrial Science and Technology, AIST Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan. libiao-han@aist.go.jp
Zhao
Chang-Qiu
CQ
Onozawa Sy
Shun-ya
SY
Goto
Midori
M
Tanaka
Masato
M
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D008968:Molecular Conformation; D009944:Organoplatinum Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D009944:Organoplatinum Compounds; D010721:Phosphinic Acids; D010165:Palladium; D006859:Hydrogen