Chiral N-phosphonyl imine chemistry: asymmetric 1,2-additions of allylmagnesium bromides

Adiseshu Kattuboina; Parminder Kaur; Thao Nguyen; Guigen Li

doi:10.1016/j.tetlet.2008.04.038

Chiral N-phosphonyl imine chemistry: asymmetric 1,2-additions of allylmagnesium bromides

Adiseshu Kattuboina, Parminder Kaur, Thao Nguyen, Guigen Li

Chemistry and Biochemistry

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

37 Scopus citations

Abstract

Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C₂-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples.

Original language	English
Pages (from-to)	3722-3724
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.038
State	Published - Jun 2 2008

Keywords

1,2-Addition
Allylmagnesium bromide
Chiral N-phosphonyl imines
Grignard reagents
Homoallylic amines

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10.1016/j.tetlet.2008.04.038

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title = "Chiral N-phosphonyl imine chemistry: asymmetric 1,2-additions of allylmagnesium bromides",

abstract = "Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C2-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples.",

keywords = "1,2-Addition, Allylmagnesium bromide, Chiral N-phosphonyl imines, Grignard reagents, Homoallylic amines",

author = "Adiseshu Kattuboina and Parminder Kaur and Thao Nguyen and Guigen Li",

year = "2008",

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journal = "Tetrahedron Letters",

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T2 - asymmetric 1,2-additions of allylmagnesium bromides

AU - Kattuboina, Adiseshu

AU - Kaur, Parminder

AU - Nguyen, Thao

AU - Li, Guigen

PY - 2008/6/2

Y1 - 2008/6/2

N2 - Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C2-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples.

AB - Chiral N-phosphonyl homoallylic amines were synthesized by the reaction of allylmagnesium bromide with chiral N-phosphonyl imines. The C2-symmetric chiral N-phosphonyl group was optimized for this reaction. Excellent yields and good diastereoselectivities were obtained for eight examples.

KW - 1,2-Addition

KW - Allylmagnesium bromide

KW - Chiral N-phosphonyl imines

KW - Grignard reagents

KW - Homoallylic amines

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