Premium
A Highly anti ‐Selective Asymmetric Henry Reaction Catalyzed by a Chiral Copper Complex: Applications to the Syntheses of (+)‐Spisulosine and a Pyrroloisoquinoline Derivative
Author(s) -
Xu Kun,
Lai Guoyin,
Zha Zhenggen,
Pan Susu,
Chen Huanwen,
Wang Zhiyong
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201775
Subject(s) - catalysis , derivative (finance) , electrospray ionization , chemistry , adduct , copper , reaction mechanism , mass spectrometry , combinatorial chemistry , medicinal chemistry , organic chemistry , chromatography , financial economics , economics
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.