Kinetic evidence for the formation of oxazolidinones in the stereogenic step of proline-catalyzed reactions

Tanja Kanzian; Sami Lakhdar; Herbert Mayr

doi:10.1002/anie.201004344

Kinetic evidence for the formation of oxazolidinones in the stereogenic step of proline-catalyzed reactions

Tanja Kanzian
, Sami Lakhdar
, Herbert Mayr

Department Chemie
Universität München

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

57 Citations (Scopus)

Résumé

Neighboring-group participation: Anchimeric assistance of the carboxylate group accelerates the attack of the electrophiles at the double bond of the proline-derived enamine A by a factor of about 50.

langue originale	Anglais
Pages (de - à)	9526-9529
Nombre de pages	4
journal	Angewandte Chemie - International Edition
Volume	49
Numéro de publication	49
Les DOIs	https://doi.org/10.1002/anie.201004344
état	Publié - 3 déc. 2010
Modification externe	Oui

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10.1002/anie.201004344

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title = "Kinetic evidence for the formation of oxazolidinones in the stereogenic step of proline-catalyzed reactions",

abstract = "Neighboring-group participation: Anchimeric assistance of the carboxylate group accelerates the attack of the electrophiles at the double bond of the proline-derived enamine A by a factor of about 50.",

keywords = "anchimeric assistance, enamine activation, kinetics, linear free energy relationships, nucleophilicity",

author = "Tanja Kanzian and Sami Lakhdar and Herbert Mayr",

year = "2010",

month = dec,

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doi = "10.1002/anie.201004344",

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T1 - Kinetic evidence for the formation of oxazolidinones in the stereogenic step of proline-catalyzed reactions

AU - Kanzian, Tanja

AU - Lakhdar, Sami

AU - Mayr, Herbert

PY - 2010/12/3

Y1 - 2010/12/3

N2 - Neighboring-group participation: Anchimeric assistance of the carboxylate group accelerates the attack of the electrophiles at the double bond of the proline-derived enamine A by a factor of about 50.

AB - Neighboring-group participation: Anchimeric assistance of the carboxylate group accelerates the attack of the electrophiles at the double bond of the proline-derived enamine A by a factor of about 50.

KW - anchimeric assistance

KW - enamine activation

KW - kinetics

KW - linear free energy relationships

KW - nucleophilicity

UR - https://www.scopus.com/pages/publications/78650154831

U2 - 10.1002/anie.201004344

DO - 10.1002/anie.201004344

M3 - Article

C2 - 21053224

AN - SCOPUS:78650154831

SN - 1433-7851

VL - 49

SP - 9526

EP - 9529

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 49

ER -

Kinetic evidence for the formation of oxazolidinones in the stereogenic step of proline-catalyzed reactions

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