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

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.",

keywords = "Enolates, N-phosphonyl imines, Phosphoramide, α-alkyl β-amino ketones",

author = "Teng Ai and Jianlin Han and Chen, \{Zhong Xiu\} and Guigen Li",

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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

Y1 - 2009/2

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

UR - https://www.scopus.com/pages/publications/58849132974

UR - https://www.scopus.com/pages/publications/58849132974#tab=citedBy

U2 - 10.1111/j.1747-0285.2008.00771.x

DO - 10.1111/j.1747-0285.2008.00771.x

M3 - Article

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AN - SCOPUS:58849132974

SN - 1747-0277

VL - 73

SP - 203

EP - 208

JO - Chemical Biology and Drug Design

JF - Chemical Biology and Drug Design

IS - 2

ER -

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

Abstract

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