New chiral ferrocenyl P,S-ligands for highly diastereo-/enantioselective catalytic [3 + 2] cycloaddition of azomethine ylides with cyclic and acyclic enones.
A new family of chiral ferrocenyl P,S-ligands has been developed and successfully applied in a highly endo-selective catalytic asymmetric cycloaddition of azomethine ylides with various enones, including cyclic and acyclic α-enones. For cyclic α-enones, a [Cu(CH(3)CN)(4)]ClO(4)/(R(c),S(Fc))-2f complex catalyzed the cycloaddition to give the sole endo-cycloadducts in perfect enantioselectivities (normally 99% ee), while an AgOAc/(R(c),S(Fc))-2f catalytic system exhibited good endo/exo selectivities (endo/exo = 91/9 to 96/4) and high enantiocontrol (up to 98% ee) for acyclic α-enones.
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
Cheng
C
Zhang
Sai-Bo
SB
Yu
Xiang-Ping
XP
Hu
Dao-Yong
DY
Wang
Zhuo
Z
Zheng
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D008024:Ligands; D013882:Thiosemicarbazones; C512188:azomethine; D010758:Phosphorus; D013455:Sulfur