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

74 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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10.1016/j.tetlet.2008.01.028

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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",

author = "Adiseshu Kattuboina and Guigen Li",

note = "Funding Information: We gratefully acknowledge the Robert A. Welch foundation (D-1361) for the generous support of this work. We thank our co-workers, Dr. Yining Wang, Parminder Kaur, Ai Teng, Aaron Olmos, and Thao Nguyen for their helpful discussions and assistance, David W. Purkiss for his assistance in NMR and Eileen Duesler (Univ. of New Mexico) for X-ray analysis.",

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doi = "10.1016/j.tetlet.2008.01.028",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Chiral N-phosphonyl imine chemistry

T2 - new reagents and their applications for asymmetric reactions

AU - Kattuboina, Adiseshu

AU - Li, Guigen

N1 - Funding Information: We gratefully acknowledge the Robert A. Welch foundation (D-1361) for the generous support of this work. We thank our co-workers, Dr. Yining Wang, Parminder Kaur, Ai Teng, Aaron Olmos, and Thao Nguyen for their helpful discussions and assistance, David W. Purkiss for his assistance in NMR and Eileen Duesler (Univ. of New Mexico) for X-ray analysis.

PY - 2008/3/3

Y1 - 2008/3/3

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.

KW - Aziridine

KW - C-Symmetric diamine

KW - N-Phosphonyl imines

KW - Phosphoramide

KW - aza-Darzens reaction

KW - aza-Henry reaction

UR - http://www.scopus.com/inward/record.url?scp=38949090994&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.01.028

DO - 10.1016/j.tetlet.2008.01.028

M3 - Article

AN - SCOPUS:38949090994

VL - 49

SP - 1573

EP - 1577

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -

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

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Keywords

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