Are sp Lithiated Carbons More Nucleophilic than sp2or sp3Ones? A Comparative DFT Study of the Condensation of Propynyllithium Aggregates on Formaldehyde-Reference-Cited by-同舟云学术

Are sp Lithiated Carbons More Nucleophilic than sp2or sp3Ones? A Comparative DFT Study of the Condensation of Propynyllithium Aggregates on Formaldehyde

Published:2010-02-08 Issue:5 Volume:75 Page:1427-1436
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Fressigné Catherine¹²,Maddaluno Jacques²

Affiliation:

1. Laboratoire de Chimie Théorique, CNRS UMR 7616, Université Pierre et Marie Curie, Case Courrier 137, 4, place Jussieu, 75252 Paris Cedex 05, France

2. Institut de Recherche en Chimie Organique Fine, CNRS UMR 6014 & FR 3038, Université de Rouen, 76821-Mont St Aignan Cedex, France

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo902315t

Reference72 articles.

1. A highly efficient and straightforward stereoselective synthesis of novel chiral α-acetylenic ketones

2. Organolithium in Asymmetric Processes

3. Sequential addition reaction of lithium acetylides and Grignard reagents to thioiminium salts from thiolactams leading to 2,2-disubstituted cyclic amines

4. Mechanism of Acylation of Lithium Phenylacetylide with a Weinreb Amide

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