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Titolo:
Intramolecular carbolithiation reactions for the preparation of azabicyclo[2.2.1] heptanes
Autore:
Coldham, I; Fernandez, JC; Price, KN; Snowden, DJ;
Indirizzi:
Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England Univ Exeter Exeter Devon England EX4 4QD , Exeter EX4 4QD, Devon, England
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 12, volume: 65, anno: 2000,
pagine: 3788 - 3795
SICI:
0022-3263(20000616)65:12<3788:ICRFTP>2.0.ZU;2-9
Fonte:
ISI
Lingua:
ENG
Soggetto:
TIN LITHIUM EXCHANGE; ANIONIC CYCLIZATIONS; ALPHA-AMINOORGANOLITHIUMS; ASYMMETRIC LITHIATION; REDUCTIVE LITHIATION; EFFICIENT SYNTHESIS; CARBANION CENTER; REAGENTS; DERIVATIVES; 7-AZABICYCLO<2.2.1>HEPTANES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
39
Recensione:
Indirizzi per estratti:
Indirizzo: Coldham, I Univ Exeter, Sch Chem, Stocker Rd, Exeter EX4 4QD, Devon, England Univ Exeter Stocker Rd Exeter Devon England EX4 4QD on, England
Citazione:
I. Coldham et al., "Intramolecular carbolithiation reactions for the preparation of azabicyclo[2.2.1] heptanes", J ORG CHEM, 65(12), 2000, pp. 3788-3795

Abstract

Tin-lithium exchange and intramolecular carbolithiation (anionic cyclization) have been used to construct the three nitrogen-positional isomers of the azabicyclo[2.2.1]heptane ring system. The 7-azabicyclo[2.2.1]heptane ringsystem is accessed from either diastereomer of a 2,5-disubstituted pyrrolidine, via a chiral organolithium intermediate. The 2-azabicyclo[2.2.1]heptane ring system is formed stereoselectively in low yield by a tandem cyclization, together with the product from monocyclization. Better yields of the 2-aza ring system can be obtained using an alternative approach from a 2-tributylstannyl-4-allylpyrrolidine, despite the trans arrangement of the tin land, hence, lithium) atom and the allyl unit. The 1-azabicyclo[2.2.1]heptane ring system is accessed in just three steps from 4-piperidone.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/04/20 alle ore 04:11:19