Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

Parminder Kaur; Gaurav Shakya; Hao Sun; Yi Pan; Guigen Li

doi:10.1039/b923914f

Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

Parminder Kaur, Gaurav Shakya, Hao Sun, Yi Pan, Guigen Li

Chemistry and Biochemistry

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Abstract

A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

Original language	English
Pages (from-to)	1091-1096
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	5
DOIs	https://doi.org/10.1039/b923914f
State	Published - 2010

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abstract = "A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.",

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T2 - An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

AU - Kaur, Parminder

AU - Shakya, Gaurav

AU - Sun, Hao

AU - Pan, Yi

AU - Li, Guigen

PY - 2010

Y1 - 2010

N2 - A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

AB - A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

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JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 5

ER -

Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

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