Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Javier Vicario; Pablo Ortiz; José M. Ezpeleta; Francisco Palacios

doi:10.1021/jo502233m

Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Javier Vicario
, Pablo Ortiz
, José M. Ezpeleta
, Francisco Palacios^*

^*Corresponding author for this work

Bioeconomy and CO2

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

46 Citations (Scopus)

Abstract

Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

Original language	English
Pages (from-to)	156-164
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	80
Issue number	1
DOIs	https://doi.org/10.1021/jo502233m
Publication status	Published - 2 Jan 2015

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title = "Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines",

abstract = "Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.",

author = "Javier Vicario and Pablo Ortiz and Ezpeleta, \{Jos{\'e} M.\} and Francisco Palacios",

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AU - Ortiz, Pablo

AU - Ezpeleta, José M.

AU - Palacios, Francisco

PY - 2015/1/2

Y1 - 2015/1/2

N2 - Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

AB - Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

UR - https://www.scopus.com/pages/publications/84937965294

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DO - 10.1021/jo502233m

M3 - Article

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AN - SCOPUS:84937965294

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

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Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Abstract

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