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The Application of a Recyclable Organocatalytic System to the Asymmetric Domino Michael/Henry Reaction in Aqueous Media
Author(s) -
Chintala Poornima,
Ghosh Subrata K.,
Long Elizabeth,
Headley Allan D.,
Ni Bukuo
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100395
Subject(s) - chemistry , domino , michael reaction , nitroaldol reaction , catalysis , aqueous medium , pyrrolidine , cascade reaction , organic chemistry , organocatalysis , aqueous solution , combinatorial chemistry , enantioselective synthesis
A new type of pyrrolidine‐based organocatalyst has been developed and found to be very effective for the domino Michael/Henry reaction in aqueous solvents. For the reaction involving pentane‐1,5‐dial and various nitroolefins, good yields (65–85%) and excellent enantioselectivities (99%) were obtained using this catalyst. In addition, the catalyst could be recycled up to four times resulting in good yields and up to seven times with good enantioselectivity.