390377-64-7

Upstream product

• 167959-92-4 (3S,4S)-4--dibenzylamino-3-hydroxy-6-methylheptanoic acid tert-butyl thioester 
• 111060-65-2 (S)-2-(dibenzylamino)-4-methylpentanal 
• 390377-24-9 tert-butyl (3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoate 

Downstream Products

• 49642-07-1 statine 

Relevant academic research and scientific papers

Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-γ-dibenzylamino-β-hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding γ-amino-β-hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-γ-tert-butoxycarbonylamino-β-hydroxy esters as the major product.

Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-statine

Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacetate-derived chiral enolates and enantiopure N,N-dibenzyl α-amino aldehydes, either the 3,4- anti or the 3,4-syn aldol adduct can be obtained with very high diastereoselectivity just by changing the chiral boron ligand configuration. The above procedure was used for a stereoselective total synthesis of (3S,4S)-statine.