Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions

Adiseshu Kattuboina; Guigen Li

doi:10.1016/j.tetlet.2008.01.028

Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions

Adiseshu Kattuboina, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

73 Scopus citations

Abstract

Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C₂-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis.

Original language	English
Pages (from-to)	1573-1577
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2008.01.028
State	Published - Mar 3 2008

Keywords

Aziridine
C-Symmetric diamine
N-Phosphonyl imines
Phosphoramide
aza-Darzens reaction
aza-Henry reaction

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title = "Chiral N-phosphonyl imine chemistry: new reagents and their applications for asymmetric reactions",

abstract = "Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C2-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis.",

keywords = "Aziridine, C-Symmetric diamine, N-Phosphonyl imines, Phosphoramide, aza-Darzens reaction, aza-Henry reaction",

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N2 - Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C2-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis.

AB - Novel chiral N-phosphonyl imines 2 have been designed and synthesized using chiral N-phosphoramide 1. These N-phosphonyl imines have been successfully utilized for asymmetric aza-Darzens reaction and asymmetric aza-Henry reaction. The C2-symmetric chiral auxiliary tolerates oxidation, is not sensitive to racemization and can be recycled for large scale synthesis.

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KW - C-Symmetric diamine

KW - N-Phosphonyl imines

KW - Phosphoramide

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KW - aza-Henry reaction

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