A highly anti-selective asymmetric Henry reaction catalyzed by a chiral copper complex: applications to the syntheses of (+)-spisulosine and a pyrroloisoquinoline derivative.
A highly anti-selective asymmetric Henry reaction has been developed, affording synthetically versatile β-nitroalcohols in a predominately anti-selective manner (mostly above 15:1) and excellent ee values (mostly above 95%). Moreover, the anti-selective Henry reaction was carried out in the presence of water for the first time with up to 99% ee. The catalytic mechanism was proposed based on the detection of the intermediates by extractive electrospray ionization mass spectrometry (EESI-MS). Furthermore, the anti adducts have been successfully transformed into the biochemically important (+)-spisulosine and a pyrroloisoquinoline derivative.
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 P.R. China.
Kun
K
Xu
Guoyin
G
Lai
Zhenggen
Z
Zha
Susu
S
Pan
Huanwen
H
Chen
Zhiyong
Z
Wang
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D007546:Isoquinolines; D008055:Lipids; D009942:Organometallic Compounds; D003300:Copper; C408363:spisulosine