» Articles » PMID: 15727473

Stereocontrolled Synthesis of Angularly Substituted 1-azabicyclic Rings by Cationic 2-aza-cope Rearrangements

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2005 Feb 25
PMID 15727473
Citations 6
Authors
Affiliations
Soon will be listed here.
Abstract

A new synthesis of 1-azabicyclic molecules having angular substitution is reported. This method can be employed to prepare a range of 1-azabicylic rings, including ones containing vicinal quaternary carbon centers and three contiguous stereocenters. [structure: see text]

Citing Articles

Lewis acidic FeCl promoted 2-aza-Cope rearrangement to afford α-substituted homoallylamines in dimethyl carbonate.

Gadde K, Daelemans J, Maes B, Abbaspour Tehrani K RSC Adv. 2022; 9(31):18013-18017.

PMID: 35520547 PMC: 9064679. DOI: 10.1039/c9ra03277k.


Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Aron Z, Ito T, May T, Overman L, Wang J J Org Chem. 2013; 78(19):9929-48.

PMID: 24090405 PMC: 3843940. DOI: 10.1021/jo4018099.


Enantioselective synthesis of angularly substituted 1-azabicyclic ring systems: dynamic kinetic resolution using aza-Cope rearrangements.

Ito T, Overman L, Wang J J Am Chem Soc. 2010; 132(10):3272-3.

PMID: 20175519 PMC: 2858009. DOI: 10.1021/ja100607z.


The Domino Way to Heterocycles.

Padwa A, Bur S Tetrahedron. 2007; 63(25):5341-5378.

PMID: 17940591 PMC: 2031872. DOI: 10.1016/j.tet.2007.03.158.


Bisphosphine-catalyzed mixed double-Michael reactions: asymmetric synthesis of oxazolidines, thiazolidines, and pyrrolidines.

Sriramurthy V, Barcan G, Kwon O J Am Chem Soc. 2007; 129(43):12928-9.

PMID: 17924625 PMC: 2536693. DOI: 10.1021/ja073754n.