112720-39-5

Usage

InChI:InChI=1/C6H13NO2.ClH/c1-6(2,3)4(7)5(8)9;/h4H,7H2,1-3H3,(H,8,9);1H/t4-;/m1./s1

Upstream product

• 68222-58-2 2-(2,2-Dimethyl-propionylamino)-3,3-dimethyl-butyric acid 
• 275800-56-1 (R)-2-(Benzyl-formyl-amino)-3,3-dimethyl-butyric acid 
• 275800-55-0 N-benzyl-N-(1-cyano-2,2-dimethyl-propyl)-formamide 
• 1775-74-2 N-(2,2-dimethylpropylidene)benzylamine 
• 283157-25-5 2-(9-fluorenylideneamino)-3,3-dimethylbutyronitrile 
• 283157-16-4 2-(9-fluorenylamino)-3,3-dimethylbutanenitrile 
• 630-19-3 pivalaldehyde 
• 189248-83-7 (R)-2-(2,2-Dimethyl-propionylamino)-3,3-dimethyl-butyric acid 

Downstream Products

• 268556-63-4 ((R)-1-Benzylcarbamoyl-2,2-dimethyl-propyl)-carbamic acid 4-nitro-phenyl ester 
• 268556-62-3 (R)-N-benzyl 2-amino-3,3-dimethylbutanamide 

Relevant academic research and scientific papers

A novel synthesis of tert-leucine via a Leuckart type reaction

An efficient synthesis of racemic tert-leucine from trimethylpyruvic acid using a Leuckart type reaction is described. A facile resolution of an intermediate with α-methylbenzylamine allows entry into either (R)- or (S)-tert-leucine.

The Strecker reaction coupled to Viedma ripening: A simple route to highly hindered enantiomerically pure amino acids

The Strecker reaction is broadly used for the preparation of α-amino acids. However, control of enantioselectivity remains challenging. We here couple the Strecker reaction to Viedma ripening for the absolute asymmetric synthesis of highly sterically hindered α-amino acids. As proof-of-principle, the enantiomerically pure α-amino acids tert-leucine and α-(1-adamantyl)glycine were obtained.

A catalytic asymmetric Strecker-type reaction promoted by Lewis acid-Lewis base bifunctional catalyst

A general asymmetric Strecker-type reaction is reported, catalyzed by the Lewis acid-Lewis base bifunctional catalyst 1. The reaction of trimethylsilyl cyanide (TMSCN) with various fluorenyl imines, including n-aldimines and α,β-unsaturated imines, proceeds with good to excellent enantioselectivities in the presence of a catalytic amount of phenol as additive (20 mol%) (catalytic system 1). The products were successfully converted to the corresponding amino acid derivatives in high yields without loss of enantiomeric purity. Furthermore, hydrogenation or dihydroxylation of the products from α,β-unsaturated imines afforded saturated or functionalized aminonitriles also without loss of enantiomeric purity. The absolute configuration of the products and a control experiment using catalyst 2 supported the proposed dual activation of the imine and TMSCN by the Lewis acid (Al) and the Lewis base moiety (phosphine oxide) of 1. From the mechanistic studies including kinetic and NMR experiments of the catalytic species, the role of PhOH seems to be a proton source to protonate the anionic nitrogen of the intermediate. Specifically, we have found that TMSCN is more reactive than HCN in this catalytic system, probably due to the activation ability of the phosphine oxide moiety of 1 toward TMSCN. This fact prompted us to develop the novel catalytic system 2, consisting of 1 (9 mol%), TMSCN (20 mol%) and HCN (1.2 mol eq). This new system afforded comparable results with obtained by system 1 (1 (9 mol%)-TMSCN (2 mol eq)-PhOH (20 mol%)).