105251-35-2

Upstream product

• 167773-12-8 2-<(2E/Z)-2-butenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-52-7 benzaldehyde 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 622-79-7 benzyl azide 
• 941278-25-7 (E)-but-2-en-1-yl tert-butyl carbonate 
• 973-59-1 2,6-di-tert-butyl-4-(benzylideneamino)phenol 
• 100-46-9 benzylamine 
• 1039032-31-9 (4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene 
• 25201-44-9 2-methyl-1-phenyl-3-butene-1-ol 

Relevant academic research and scientific papers

Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.

Characterization and utility of N-unsubstituted imines synthesized from alkyl azides by ruthenium catalysis

Shine a light: A fluorescent light-induced synthetic method for the title compounds has been developed and the chemoselective nature of the reaction is highlighted by the observation of the cis/trans isomers of various N-unsubstituted imines. The synthetic utility of this method is demonstrated by the one-pot imine formation/asymmetric allylation sequence of benzyl azide catalyzed by 1. (Ipc=isopinocampheyl). Copyright

α-aminoallylation of aldehydes with ammonia: Stereoselective synthesis of homoallylic primary amines

Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon α-amino acid, alloisoleucine, was achieved utilizing this reaction. Copyright

Diastereoselective Addition of Crotylboronates to Oximes

The addition of E- and Z-crotylboronates 8,9 to aldoximes has been realized in good yields by running the reaction under 4-9 kbar pressure.The direction of the attendant diastereoselectivity was surprising: E-8 led preferentially to the anti-, Z-9 to the syn-N-(β-methylalkyl)hydroxylamines 10, 11.