Double-Mannich annulation of cyclic ketones using N,N-Bis(ethoxymethyl)alkylamine reagents.
[Structure: see text] N,N-Bis(ethoxymethyl)alkylamines function as effective reagents in the double-Mannich annulation of cyclic ketone substrates, providing efficient access to a series of azabicyclic ketones. These ring systems are a useful scaffold for the four-step synthesis of novel constrained homocholine analogues.
Halliday
Jill I
JI
School of Chemistry, F11, and Faculty of Pharmacy, A15, University of Sydney, Camperdown, NSW 2006, Australia.
Chebib
Mary
M
Turner
Peter
P
McLeod
Malcolm D
MD
D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002794:Choline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000588:Amines; D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007659:Ketones; C007954:homocholine; D002794:Choline