Imidazolidinone-derived enamines: Nucleophiles with low reactivity

Sami Lakhdar; Biplab Maji; Herbert Mayr

doi:10.1002/anie.201201240

Imidazolidinone-derived enamines: Nucleophiles with low reactivity

Sami Lakhdar
, Biplab Maji
, Herbert Mayr

Universität München
Department Chemie

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

55 Citations (Scopus)

Résumé

Extraordinarily weak nucleophiles: Enamines derived from imidazolidinones are 10 ³-10 ⁵ times less reactive than those derived from the Hayashi-Jørgensen catalyst. This finding explains the lower activity of MacMillan catalysts for enamine-activated reactions.

langue originale	Anglais
Pages (de - à)	5739-5742
Nombre de pages	4
journal	Angewandte Chemie - International Edition
Volume	51
Numéro de publication	23
Les DOIs	https://doi.org/10.1002/anie.201201240
état	Publié - 4 juin 2012
Modification externe	Oui

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10.1002/anie.201201240

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title = "Imidazolidinone-derived enamines: Nucleophiles with low reactivity",

abstract = "Extraordinarily weak nucleophiles: Enamines derived from imidazolidinones are 10 3-10 5 times less reactive than those derived from the Hayashi-J{\o}rgensen catalyst. This finding explains the lower activity of MacMillan catalysts for enamine-activated reactions.",

keywords = "enamines, kinetics, linear free energy relationships, nucleophilicity, pyramidalization",

author = "Sami Lakhdar and Biplab Maji and Herbert Mayr",

year = "2012",

month = jun,

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doi = "10.1002/anie.201201240",

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T1 - Imidazolidinone-derived enamines

T2 - Nucleophiles with low reactivity

AU - Lakhdar, Sami

AU - Maji, Biplab

AU - Mayr, Herbert

PY - 2012/6/4

Y1 - 2012/6/4

N2 - Extraordinarily weak nucleophiles: Enamines derived from imidazolidinones are 10 3-10 5 times less reactive than those derived from the Hayashi-Jørgensen catalyst. This finding explains the lower activity of MacMillan catalysts for enamine-activated reactions.

AB - Extraordinarily weak nucleophiles: Enamines derived from imidazolidinones are 10 3-10 5 times less reactive than those derived from the Hayashi-Jørgensen catalyst. This finding explains the lower activity of MacMillan catalysts for enamine-activated reactions.

KW - enamines

KW - kinetics

KW - linear free energy relationships

KW - nucleophilicity

KW - pyramidalization

UR - https://www.scopus.com/pages/publications/84861612128

U2 - 10.1002/anie.201201240

DO - 10.1002/anie.201201240

M3 - Article

AN - SCOPUS:84861612128

SN - 1433-7851

VL - 51

SP - 5739

EP - 5742

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

Imidazolidinone-derived enamines: Nucleophiles with low reactivity

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