Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism

Josep Comelles; Alex Pericas; Marcial Moreno-Mañas; Adelina Vallribera; Galí Drudis-Solé; Agusti Lledos; Teodor Parella; Anna Roglans; Santiago García-Granda; Laura Roces-Fernández

doi:10.1021/jo0622678

Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism

Josep Comelles
, Alex Pericas
, Marcial Moreno-Mañas
, Adelina Vallribera
, Galí Drudis-Solé
, Agusti Lledos
, Teodor Parella
, Anna Roglans
, Santiago García-Granda
, Laura Roces-Fernández

Department of Chemistry

Autonomous University of Barcelona
University of Oviedo

Research output: Contribution to journal › Scientific article › peer-review

91 Citations (Scopus)

Abstract

High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.

Original language	English
Pages (from-to)	2077-2087
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	72
Issue number	6
DOIs	https://doi.org/10.1021/jo0622678
Publication status	Published - 16 Mar 2007

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Comelles, J., Pericas, A., Moreno-Mañas, M., Vallribera, A., Drudis-Solé, G., Lledos, A., Parella, T., Roglans, A., García-Granda, S., & Roces-Fernández, L. (2007). Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism. Journal of Organic Chemistry, 72(6), 2077-2087. https://doi.org/10.1021/jo0622678

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title = "Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism",

abstract = "High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.",

author = "Josep Comelles and Alex Pericas and Marcial Moreno-Ma{\~n}as and Adelina Vallribera and Gal{\'i} Drudis-Sol{\'e} and Agusti Lledos and Teodor Parella and Anna Roglans and Santiago Garc{\'i}a-Granda and Laura Roces-Fern{\'a}ndez",

year = "2007",

month = mar,

day = "16",

doi = "10.1021/jo0622678",

language = "English",

volume = "72",

pages = "2077--2087",

journal = "Journal of Organic Chemistry",

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Comelles, J, Pericas, A, Moreno-Mañas, M, Vallribera, A, Drudis-Solé, G, Lledos, A, Parella, T, Roglans, A, García-Granda, S & Roces-Fernández, L 2007, 'Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism', Journal of Organic Chemistry, vol. 72, no. 6, pp. 2077-2087. https://doi.org/10.1021/jo0622678

TY - JOUR

T1 - Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox

T2 - The mechanism

AU - Comelles, Josep

AU - Pericas, Alex

AU - Moreno-Mañas, Marcial

AU - Vallribera, Adelina

AU - Drudis-Solé, Galí

AU - Lledos, Agusti

AU - Parella, Teodor

AU - Roglans, Anna

AU - García-Granda, Santiago

AU - Roces-Fernández, Laura

PY - 2007/3/16

Y1 - 2007/3/16

N2 - High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.

AB - High enantioselection is obtained in Michael additions of cyclic β-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and β-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.

UR - https://www.scopus.com/pages/publications/33947225755

U2 - 10.1021/jo0622678

DO - 10.1021/jo0622678

M3 - Scientific article

AN - SCOPUS:33947225755

SN - 0022-3263

VL - 72

SP - 2077

EP - 2087

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Highly enantioselective electrophilic amination and Michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox: The mechanism

Abstract

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