Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/30440
Title: Highly efficient asymmetric michael reaction of aldehydes to nitroalkenes with diphenylperhydroindolinol silyl ethers as organocatalysts
Authors: Luo, RS
Weng, J
Ai, HB
Lu, G
Chan, ASC
Keywords: Asymmetric catalysis
Michael addition
Nitroalkenes
Organocatalysis
Perhydroindolinols
Issue Date: 2009
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2009, v. 351, no. 14-15, p. 2449-2459 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asymmetric Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)Diphenylperhydroindolinol silyl ether 10 facilitated the reaction of a wide range of aldehyde and nitroalkene substrates, providing Michael adducts in nearly optically pure form (99% ee), good yields and high diastereoselectivities (synlanti up to 99:1). These re-suits show for the first time that perhydroindole derivatives can also be highly efficient organocatalysts for the asymmetric Michael reaction, exhibiting comparable or even better enantioselectivities than proline derivatives.
URI: http://hdl.handle.net/10397/30440
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.200900355
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