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

Universität München

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

57 Citations (Scopus)

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.

Original language	English
Pages (from-to)	9526-9529
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	49
DOIs	https://doi.org/10.1002/anie.201004344
Publication status	Published - 3 Dec 2010
Externally published	Yes

Keywords

anchimeric assistance
enamine activation
kinetics
linear free energy relationships
nucleophilicity

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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,

day = "3",

doi = "10.1002/anie.201004344",

language = "English",

volume = "49",

pages = "9526--9529",

journal = "Angewandte Chemie - International Edition",

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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

Abstract

Keywords

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