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Volumn , Issue 24, 2007, Pages 2509-2511

Organocatalytic enantioselective aza-Michael reaction of nitrogen heterocycles and α,β-unsaturated aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; NITROGEN; ORGANIC COMPOUND;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ATOM; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 34250214980 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b700831g Document Type: Article

Times cited : (71)

References (16)

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- One example of an amine-catalyzed aziridination of α,β- unsaturated aldehydes via a stepwise aza-Michael reaction, followed by intramolecular nucleophilic substitution, has also been reported:
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- After this manuscript was submitted, Córdova and co-workers reported the organocatalytic asymmetric aza-Michael reaction of N-carbamoylhydroxylamines to α,β-unsaturated aldehydes and the group of Jørgensen reported the enantioselective conjugate addition of nitrogen heterocycles to the same kind of aldehydes, both using diarylprolinol silyl ethers as catalysts:
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14
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- and references therein A first screening of several amine catalysts indicated that, although the reaction proceeded efficiently at RT, leading to the formation of the aza-Michael adduct in yields ranging from 20 to 95%, very low enantioselectivities (<5% ee) were obtained in all cases Other representative examples: l-proline (12% ee), l-proline methyl ester (16% ee), l-prolinol (12% ee), l-prolinol tert-butyldimethylsilyl ether (6% ee), (S)-2-(diphenylmethyl)pyrrolidine (0% ee) The electronic effect of tetrazole C-aryl substituents in promoting nucleophilic reactions preferably at N2 is known:
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