An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich Reaction

Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n = 2-5) to...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 3; pp. 493 - 497
Main Authors Mityuk, Andrey P., Denisenko, Aleksandr V., Dacenko, Oleksandr P., Grygorenko, Oleksandr O., Mykhailiuk, Pavel K., Volochnyuk, Dmitriy M., Shishkin, Oleg V., Tolmacheva, Andrey A.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ETHERS
annulation
bicyclic compounds
chlorotrimethylsilane
DRUG DISCOVERY
Mannich bases
molecular rigidity
Online AccessGet more information

Cover

More Information
Summary:Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n = 2-5) to be obtained in good yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1217137