A C(2)-symmetric chiral bis-sulfoxide ligand in a rhodium-catalyzed reaction: asymmetric 1,4-addition of sodium tetraarylborates to chromenones.
A new C(2)-symmetric chiral bis-sulfoxide ligand, (R,R)-1,2-bis(tert-butylsulfinyl)benzene, has been designed and prepared by the reaction of (R)-benzyl tert-butylsulfoxide with (R)-thiosulfinate. This ligand exhibits excellent enantioselectivities in the Rh-catalyzed asymmetric 1,4-addition reaction. In particular, the present work has realized access to optically pure flavanones for the first time through 1,4-addition of arylboronic reagents to chromenones.
Chen
Jun
J
National Engineering Research Center of Chiral Drugs and Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Chen
Junmin
J
Lang
Feng
F
Zhang
Xiangyang
X
Cun
Linfeng
L
Zhu
Jin
J
Deng
Jingen
J
Liao
Jian
J
D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry*
D001881:Borates; D002867:Chromones; D008024:Ligands; D009942:Organometallic Compounds; D013454:Sulfoxides; D012238:Rhodium