Organic Letters 2011-04-01

Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis.

Michael J Brown, Guy J Clarkson, Graham G Inglis, Michael Shipman

Index: Org. Lett. 13(7) , 1686-9, (2011)

Full Text: HTML

Abstract

An efficient two-step synthesis of a wide range of 3-methylene-1,2-diazetidines has been developed through application of a Cu(I)-catalyzed 4-exo ring closure. The double bond of this new class of strained heterocycle can be functionalized in a stereocontrolled manner by using palladium-catalyzed Heck reactions. Moreover, chemoselective reduction of 3-alkylidene-1,2-diazetidines gives access to saturated 1,2-diazetidines and vicinal diamines.

Related Compounds

  • Azetidine

Related Articles:

Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.

2012-08-17

[Org. Lett. 14(16) , 4174-7, (2012)]

Identification of spirocyclic piperidine-azetidine inverse agonists of the ghrelin receptor.

2012-07-01

[Bioorg. Med. Chem. Lett. 22(13) , 4281-7, (2012)]

Complex N-heterocycle synthesis via iron-catalyzed, direct C-H bond amination.

2013-05-03

[Science 340(6132) , 591-5, (2013)]

Chemistry and pharmacology of nicotinic ligands based on 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol (AMOP-H-OH) for possible use in depression.

2009-08-01

[ChemMedChem 4(8) , 1279-91, (2009)]

Fatty acid amide hydrolase inhibitors. Surprising selectivity of chiral azetidine ureas.

2009-08-01

[Bioorg. Med. Chem. Lett. 19(15) , 4241-4, (2009)]

More Articles...