Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α-alkyl β-amino ketones by reacting phosphonyl imines with ketone-derived enolates

Teng Ai; Jianlin Han; Zhong Xiu Chen; Guigen Li

doi:10.1111/j.1747-0285.2008.00771.x

Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α-alkyl β-amino ketones by reacting phosphonyl imines with ketone-derived enolates

Teng Ai, Jianlin Han, Zhong Xiu Chen, Guigen Li

Center for Drug Design

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

30 Scopus citations

Abstract

A series of new chiral syn-α-branched β-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.

Original language	English (US)
Pages (from-to)	203-208
Number of pages	6
Journal	Chemical Biology and Drug Design
Volume	73
Issue number	2
DOIs	https://doi.org/10.1111/j.1747-0285.2008.00771.x
State	Published - Feb 1 2009

Keywords

Enolates
N-phosphonyl imines
Phosphoramide
α-alkyl β-amino ketones

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10.1111/j.1747-0285.2008.00771.x

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abstract = "A series of new chiral syn-α-branched β-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.",

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doi = "10.1111/j.1747-0285.2008.00771.x",

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T2 - Asymmetric synthesis of α-alkyl β-amino ketones by reacting phosphonyl imines with ketone-derived enolates

AU - Ai, Teng

AU - Han, Jianlin

AU - Chen, Zhong Xiu

AU - Li, Guigen

PY - 2009/2/1

Y1 - 2009/2/1

N2 - A series of new chiral syn-α-branched β-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.

AB - A series of new chiral syn-α-branched β-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.

KW - Enolates

KW - N-phosphonyl imines

KW - Phosphoramide

KW - α-alkyl β-amino ketones

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Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α-alkyl β-amino ketones by reacting phosphonyl imines with ketone-derived enolates

Abstract

Keywords

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