127258-28-0

Upstream product

• 1191-15-7 diisobutylaluminium hydride 
• 100-47-0 benzonitrile 

Downstream Products

• 81880-29-7 2-methyl-1-phenyl-butylamin; hydrochloride 
• 1217456-02-4 C₁₅H₂₁NO₄ 

Relevant academic research and scientific papers

Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess

A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

(E)-2-boryl 1,3-dienes from the 10-TMS-9-BBDs: Highly selective reagents for the asymmetric synthesis of anti-α,β-disubstituted β-allenylamines from the allylboration of aldimines

The asymmetric allylboration of N-H aldimines with optically pure trans-4-substituted-2-boryl-1,3-dienes 6 is described. These organoboranes 6 serve as near-perfect asymmetric allylborating agents for N-H aldimines for the preparation of anti-1,2-disubstituted-3,4-pentadien-1-amines 11 as essentially single diastereomers in enantiomerically pure form (>98% de, ≥98% ee). Enantiomerically pure cis-2,3-disubstitued piperidines 12 and α,β-disubstituted-β-amino acids 17 are readily prepared through the standard protocols. A novel Ru-catalyzed hydroamination provides trans-4,5-disubstituted-1-pyrrolines 21 from 11.

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.