Chiral N-Phosphonyl Imine Chemistry: Asymmetric Aza-Henry Reaction

A series of chiral N-phosphonyl imines have been synthesized and utilized successfully in asymmetric aza-Henry reaction. The chiral auxiliary was optimized for this reaction by varying different R groups on the nitrogen atoms. The reaction is convenient to perform to give excellent yields and good d...

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Bibliographic Details
Published in:Chemical biology & drug design 2008-03, Vol.71 (3), p.216-223
Main Authors: Kattuboina, Adiseshu, Kaur, Parminder, Ai, Teng, Li, Guigen
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
aza-Henry reaction
chiral N-phosphonyl imines
chiral phosphoramide
Imines - chemistry
Stereoisomerism
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Summary:A series of chiral N-phosphonyl imines have been synthesized and utilized successfully in asymmetric aza-Henry reaction. The chiral auxiliary was optimized for this reaction by varying different R groups on the nitrogen atoms. The reaction is convenient to perform to give excellent yields and good diastereoselectivities. The absolute stereochemistry was unambiguously determined by converting a resulting vicinal nitroamine into its N-Boc derivative which serves as a known compound.
ISSN:1747-0277
1747-0285
DOI:10.1111/j.1747-0285.2008.00633.x