604788-98-9

Upstream product

• 604788-97-8 (3R,4S)-4-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-phenyl)-piperidin-2-yl]-3-methoxy-1-p-tolyl-azetidin-2-one 
• 657394-10-0 (3R,4S)-4-[(2S,4R)-1-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-piperidin-2-yl]-3-methoxy-1-p-tolyl-azetidin-2-one 
• 657394-28-0 (3R,4S)-4-((2S,4R)-1-Allyl-4-hydroxy-piperidin-2-yl)-3-methoxy-1-p-tolyl-azetidin-2-one 
• 657394-27-9 (S)-1-Allyl-2-((2S,3R)-3-methoxy-4-oxo-1-p-tolyl-azetidin-2-yl)-piperidin-4-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 383883-66-7 (+)-(3R,4R)-4-formyl-3-methoxy-1-(p-tolyl)-2-azetidinone 
• 383883-65-6 2-(3-methoxy-4-oxo-1-p-tolyl-azetidin-2-yl)-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one 
• 604788-96-7 (3R,4S)-4-[(2S,4R)-4-Hydroxy-1-(4-methoxy-phenyl)-piperidin-2-yl]-3-methoxy-1-p-tolyl-azetidin-2-one 
• 604788-95-6 (S)-2-((2S,3R)-3-Methoxy-4-oxo-1-p-tolyl-azetidin-2-yl)-1-(4-methoxy-phenyl)-piperidin-4-one 
• 383883-64-5 (3R,4S)-3-Methoxy-4-{[(E)-4-methoxy-phenylimino]-methyl}-1-p-tolyl-azetidin-2-one 

Downstream Products

• 383883-57-6 (1S,2R,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-1-p-tolylamino-hexahydro-indolizin-3-one 

Relevant academic research and scientific papers

Chemoselective deprotection of allylic amines catalyzed by Grubbs' carbene

A commercially available ruthenium complex (first generation Grubbs' carbene) was used for the catalytic deprotection of allylic amines (secondary as well as tertiary), by using for the first time reagents different from palladium catalysts. Interestingly, the catalytic system directs the reaction toward the selective deprotection of allylamines in the presence of allylic ethers.

Ruthenium-Catalyzed Chemoselective N-Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic Amines

A novel application of the Grubbs carbene complex has been discovered. The first examples of the catalytic deprotection of allylic amines with reagents other than palladium catalysts have been achieved through Grubbs carbene mediated reaction. Significantly, the catalytic system directs the reaction toward the selective deprotection of allylic amines (secondary as well as tertiary) in the presence of allylic ethers. A variety of substrates, including enantiomerically pure multifunctional piperidines, are also usable. The new method is more convenient, chemoselective, and operationally simple than the palladium-catalyzed method. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that the reactive species involved in the reaction may be an Ru-H species rather than the Grubbs carbene itself. Thus, the isomerization may occur according to the hydride mechanism. The synthetic utility of this ruthenium-catalyzed allyl cleavage is illustrated by the preparation of indolizidine-type alkaloids.

Useful dual Diels-Alder behavior of 2-azetidinone-tethered aryl imines as azadienophiles or azadienes: A β-lactam-based stereocontrolled access to optically pure highly functionalized indolizidine systems

Imines derived from 4-oxoazetidine-2-carbaldehydes have been found to be versatile Diels - Alder reagents in that they exhibit two reactivity patterns. 2-Azetidinone-tethered imines undergo diastereoselective reaction with Danishefsky's diene in the prese

Dual behavior of 2-azetidinone-tethered arylimines as azadienophiles or azadienes. Application to the asymmetric synthesis of indolizidine-type systems

The first methodology to prepare indolizidine systems directly from β-lactams has been developed. This process involves the amide bond cleavage of the β-lactam ring in the aza Diels-Alder cycloadducts with concomitant cyclization. Indolizidinone precursor