Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles

Guillaume Dagousset; Kohei Moriya; Rasmus Mose; Guillaume Berionni; Paul Knochel

doi:10.1002/anie.201308679

Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles

Guillaume Dagousset, Kohei Moriya, Rasmus Mose, Guillaume Berionni, Paul Knochel

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

Résumé

A practical stereoselective iodide-lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open-chain molecules.

langue originale	Anglais
Pages (de - à)	1425-1429
Nombre de pages	5
journal	Angewandte Chemie - International Edition
Volume	53
Numéro de publication	5
Les DOIs	https://doi.org/10.1002/anie.201308679
Etat de la publication	Publié - 27 janv. 2014
Modification externe	Oui

Accès au document

10.1002/anie.201308679

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Link to publication in Scopus

CCDC 963930: Experimental Crystal Structure Determination
Berionni, G. (Contributeur), Dagousset, G. (Contributeur), Karaghiosoff, K. (Contributeur), Knochel, P. (Contributeur), Moriya, K. (Contributeur) & Mose, R. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2013
DOI: 10.5517/cc11c1jz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11c1jz&sid=DataCite
Ensemble de données
CCDC 963929: Experimental Crystal Structure Determination
Berionni, G. (Contributeur), Dagousset, G. (Contributeur), Karaghiosoff, K. (Contributeur), Knochel, P. (Contributeur), Moriya, K. (Contributeur) & Mose, R. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2013
DOI: 10.5517/cc11c1hy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11c1hy&sid=DataCite
Ensemble de données

Contient cette citation

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title = "Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles",

abstract = "A practical stereoselective iodide-lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open-chain molecules.",

keywords = "Acylation, Diastereoselectivity, Kinetics, Lithiation, Nucleophilic substiution",

author = "Guillaume Dagousset and Kohei Moriya and Rasmus Mose and Guillaume Berionni and Paul Knochel",

year = "2014",

month = jan,

day = "27",

doi = "10.1002/anie.201308679",

language = "English",

volume = "53",

pages = "1425--1429",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "5",

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TY - JOUR

T1 - Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles

AU - Dagousset, Guillaume

AU - Moriya, Kohei

AU - Mose, Rasmus

AU - Berionni, Guillaume

AU - Knochel, Paul

PY - 2014/1/27

Y1 - 2014/1/27

N2 - A practical stereoselective iodide-lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open-chain molecules.

AB - A practical stereoselective iodide-lithium exchange was used in the first general preparation of functionalized stereodefined acyclic secondary nonstabilized lithium reagents from the corresponding secondary alkyl iodides. These lithium reagents react with various electrophiles including carbon electrophiles with high retention of configuration. Kinetic data on the configurational stability of these acyclic alkyllithium reagents are given. This methodology offers a new entry to chiral synthons for the stereoselective synthesis of open-chain molecules.

KW - Acylation

KW - Diastereoselectivity

KW - Kinetics

KW - Lithiation

KW - Nucleophilic substiution

UR - http://www.scopus.com/inward/record.url?scp=84893962238&partnerID=8YFLogxK

U2 - 10.1002/anie.201308679

DO - 10.1002/anie.201308679

M3 - Article

AN - SCOPUS:84893962238

SN - 1433-7851

VL - 53

SP - 1425

EP - 1429

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Diastereoselective synthesis of open-chain secondary alkyllithium compounds and trapping reactions with electrophiles

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Ensembles de données

CCDC 963930: Experimental Crystal Structure Determination

CCDC 963929: Experimental Crystal Structure Determination

Contient cette citation