121731-62-2

Upstream product

• 121731-60-0 1-isopropyl-2-propenylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 115378-34-2 (3S)-3-(tert-butoxycarbonylamino)-4-methyl-1-pentene 
• 79069-51-5 (S)-N-tert-butoxycarbonylvalinal 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 

Downstream Products

• 121731-80-4 (1S,4R,8R)-trans-1,3,4,4a,5,7,8,8a-octahydro-1-isopropyl-2-(p-tolylsulfonyl)-6(2H)-isoquinolone 
• 121731-81-5 (1S,4S,8R)-cis-1,3,4,4a,5,7,8,8a-octahydro-1-isopropyl-2-(p-tolylsulfonyl)-6(2H)-isoquinolone 
• 121731-70-2 N-<5-<(tert-butyldimethylsilyl)oxy>-3(E),5-hexadienyl>-N-<(1'S)-1'-isopropyl-2'-propenyl>-p-toluenesulfonamide 
• 121731-68-8 N-<5-oxo-3(E)-hexenyl>-N-<(1'S)-1'-isopropyl-2'-propenyl>-p-toluenesulfonamide 
• 121731-66-6 N-(2-formylethyl)-N-<(1'S)-1'-isopropyl-2'-propenyl>-p-toluenesulfonamide 
• 121731-64-4 ethyl 3-amino>propanoate 

Relevant academic research and scientific papers

Dual Palladium(II)/Tertiary Amine Catalysis for Asymmetric Regioselective Rearrangements of Allylic Carbamates

The streamlined catalytic access to enantiopure allylic amines as valuable precursors towards chiral β- and γ-aminoalcohols as well as α- and β-aminoacids is desirable for industrial purposes. In this article an enantioselective method is described that transforms achiral allylic alcohols and N-tosylisocyanate in a single step into highly enantioenriched N-tosyl protected allylic amines via an allylic carbamate intermediate. The latter is likely to undergo a cyclisation-induced [3,3]-rearrangement catalysed by a planar chiral pentaphenylferrocene palladacycle in cooperation with a tertiary amine base. The otherwise often indispensable activation of palladacycle catalysts by a silver salt is not required in the present case and there is also no need for an inert gas atmosphere. To further improve the synthetic value, the rearrangement was used to form dimethylaminosulfonyl-protected allylic amines, which can be deprotected under non-reductive conditions.

Synthesis of the Chiral (8S)-7-Aza-1,3(E),9-decatriene System from Natural α-Amino Acids and Its Intramolecular Diels-Alder Reaction Directed toward Chiral trans-Hydroisoquinolones

L-Alanine and L-valine were converted into optically active 7-aza-1,3(E),9-decatrienes containing a (tert-butyldimethylsilyl)oxy group at C(2) and a methyl or isopropyl group at C(8).Intramolecular thermal cycloaddition reactions of these trienes gave optically active trans-nonahydro-6(2H)-isoquinolones.The relatively bulky isopropyl group at C(8) increased the trans selectivity in the ring closure.These results are in contrast with literature reports on ring closure of analogous aza trienes that lack the (tert-butyldimethylsilyl)oxy group at C(2), whichgive predominantly cis-fused rings.