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Structure‐Reactivity Studies of Simple 4‐Hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins
Author(s) -
Watts John,
Luu Lien,
McKee Vickie,
Carey Ed,
Kelleher Fintan
Publication year - 2012
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.201100028
Subject(s) - chemistry , michael reaction , conjugate , aldehyde , reactivity (psychology) , catalysis , organocatalysis , organic chemistry , addition reaction , enantioselective synthesis , medicine , mathematical analysis , alternative medicine , mathematics , pathology
Abstract A series of simple 4‐hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti ) and enantioselectivity (98% ee for syn ). Furthermore, the use of low catalyst loadings (5 mol%) and a low aldehyde molar excess (1.5 equivalents) were achieved.