Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

Zhong Xiu Chen; Teng Ai; Parminder Kaur; Guigen Li

doi:10.1016/j.tetlet.2008.12.093

Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

Zhong Xiu Chen
, Teng Ai
, Parminder Kaur
, Guigen Li

Center for Drug Design

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

29 Scopus citations

Abstract

Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral β-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.

Original language	English (US)
Pages (from-to)	1079-1081
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.093
State	Published - Mar 4 2009

Keywords

Dimethyl malonate
N-Phosphonyl imines
Phosphoramide
β-Aminomalonates

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10.1016/j.tetlet.2008.12.093

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title = "Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates",

abstract = "Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral β-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.",

keywords = "Dimethyl malonate, N-Phosphonyl imines, Phosphoramide, β-Aminomalonates",

author = "Chen, \{Zhong Xiu\} and Teng Ai and Parminder Kaur and Guigen Li",

year = "2009",

month = mar,

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doi = "10.1016/j.tetlet.2008.12.093",

language = "English (US)",

volume = "50",

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TY - JOUR

T1 - Chiral N-phosphonyl imine chemistry

T2 - asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

AU - Chen, Zhong Xiu

AU - Ai, Teng

AU - Kaur, Parminder

AU - Li, Guigen

PY - 2009/3/4

Y1 - 2009/3/4

N2 - Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral β-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.

AB - Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral β-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.

KW - Dimethyl malonate

KW - N-Phosphonyl imines

KW - Phosphoramide

KW - β-Aminomalonates

UR - https://www.scopus.com/pages/publications/58149503411

UR - https://www.scopus.com/pages/publications/58149503411#tab=citedBy

U2 - 10.1016/j.tetlet.2008.12.093

DO - 10.1016/j.tetlet.2008.12.093

M3 - Article

AN - SCOPUS:58149503411

SN - 0040-4039

VL - 50

SP - 1079

EP - 1081

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

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