110216-57-4

Upstream product

• 154228-41-8 (2S)-3-methyl-2-((1S)-1-phenylbut-3-enylamino)butan-1-ol 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 107-05-1 3-chloroprop-1-ene 
• 2622-05-1 allylmagnesium bromide 
• 688-61-9 Triallylborane 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 100-47-0 benzonitrile 
• 106356-53-0 B-allyldiisopinocampheylborane 
• 910545-65-2 (1R,3R,4S)-3-allyl-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 100-52-7 benzaldehyde 
• 84983-97-1 N-benzylidene-L-valinol 
• 88691-30-9 N-benzylidene-O-methyl-L-valinol 

Downstream Products

• 867193-39-3 ethyl 2-({[(1S)-1-phenylbut-3-enyl]amino}methyl)acrylate 
• 949021-19-6 (S)-N-(1-phenyl-3-buten-1-yl)propenamide 
• 135865-77-9 (S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine 
• 1449466-90-3 (S)-N-(t-butoxycarbonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-phenyl-butan-1-amine 

Relevant academic research and scientific papers

Enantioselective synthesis of homoallylamines by nucleophilic addition of chirally modified allylboron reagents to imines

N-silylated imines are well-suited for reaction with chirally modified allylboron reagents to give enantiomerically enriched primary homoallylamines in high yields [Eq. (a)]. The chiral ligand, here N-tosyl-(-)-norephedrin, can be recovered after the reaction and used again to generate the chiral allylboron reagent. Ts = p-toluenesulfonyl.

Enantioselective synthesis of optically active homoallylamines by allylboration of N-diisobutylaluminum imines

Diisobutylaluminum hydride (DIBAL-H) reduces nitriles to give N-diisobutylaluminum imines, which were asymmetrically allylated with chirally modified allylboron reagents. The corresponding chiral primary homoallylamines were obtained with up to 87% ee.

Asymmetric synthesis of homoallylamines by nucleophilic addition of chirally modified allylboron reagent to N-borylimines

One pot synthesis of enantioenriched homoallylamines from nitriles is described. Chirally modified allylboron reagents reacted with N-borylimines derived from partial reduction of nitriles with LiEt3BH to afford enantioenriched homoallylamines

Convenient synthesis of stable aldimine - Borane complexes, chiral δ-amino alcohols, and γ-substituted GABA analogues from nitriles

A one-pot synthesis of stable aldimine-trialkylborane adducts, the first synthesis of C- and N-deuterated imine-borane complexes, and their application for a highly enantioselective (84-99% ee) synthesis of δ-amino alcohols and γ-substituted γ-aminobutyri

Indium-mediated diastereoselective addition of allyl bromides to enantiomerically pure N-tert-butylsulfinyl aldimines

The reaction of different N-tert-butylsulfinyl aldimines 1 with allyl bromides 2 and indium powder in THF at 60°C affords, after hydrolysis with water, the corresponding N-tert-butylsulfinylamines 3 with high chemical yields and diastereoselectivities.

Enantioselective addition of chirally modified allylboranes to N-(trimethylsilyl)benzaldehyde imine

Enantioselective allylation of N-(trimethylsilyl)benzaldehyde imine has been investigated by the use of optically active allylboron reagents including dialkyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylates (1) and B-allyldiisopinocampheylborane (2) to giv

Enantioselective Synthesis of Homoallylic Amines by Addition of Allylmetal Reagents to Imines Derived from (S)-Valine Esters

Grignard and Barbier procedures have been applied to the addition of allylmethal (Zn, Cu, Pb, Bi, Al, In) species to imines derived from (S)-valine esters, principally the methyl ester.The Zn-mediated, CeCl3- or SnCl2-catalyzed "Barbier" reactions of the

Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.

Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.