159116-87-7

Upstream product

• 875-74-1 (R)-phenylglycine 
• 64715-85-1 (R)-2-methoxy-1-phenylethylamine 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 159117-08-5 [(R)-1-((R)-2-Methoxy-1-phenyl-ethylamino)-2-methyl-propyl]-phosphonic acid diethyl ester 
• 170811-29-7 (1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-2-methyl-1-phenylpropylamine 
• 676460-36-9 ethyl (3S)-2,2-difluoro-3-{N-[(1R)-(2-methoxy-1-phenylethyl)]amino}-4-methylpentanoate 
• 171227-49-9 (1R,1'R)-N-(2'-methoxy-1'-phenylethyl)-1,2-dimethylpropylamine 

Relevant academic research and scientific papers

SmI2-Mediated Reduction of γ,γ-Difluoro-α ,β-enoates with Application to the Synthesis of Functionalized (Z)-Fluoroalkene-Type Dipeptide Isosteres

A samarium diiodide (SmI2)-mediated reduction of γ,γ-difluoro-α,β-enoates (15, 29, and 34) was successfully applied to the synthesis of (Z)-fluoroalkene dipeptide isosteres (23, 30, and 35), which have served as potential dipeptide mimetics. Reduction of the γ,γ-difluoro-α,β-enoates by SmI2 proceeded via successive two-electron transfers to form dienolate species which upon kinetically controlled trapping with t-BuOH yielded Xaa-Gly-type fluoroalkene isosteres exemplified by 23, 30, and 35. Replacement of the t-BuOH kinetic trapping agent with aldehydes or ketones provided access to α-substituted fluoroalkene isosteres (43 and 45) through aldol reactions of Sm-dienolates with the carbonyl compounds. Of particular note, the use of the SmI2-HCHO reagent system with chiral enoate 34 provided D-Phe-ψ [(Z)-CF=CH]-D/L-Ser isosteres (45), which could be converted to enantiomerically pure isosteres (49-52) that bore a variety of side chain functionalities at the α-position. This was achieved by a sequence of manipulations consisting of β-lactone formation followed by chromatographic separation and ring-opening with soft nucleophiles. Included in the present work is the first utilization of a Rh-catalyzed Reformatsky reaction of chiral imines for the stereoselective preparation of α,α-difluoro-β-amino acid derivatives (28 and 33). The appropriate choice of reagents (carbonyl compounds for kinetic trapping or ring-opening nucleophiles and imines for Reformatsky reactions) allows the presented methodology to yield various fluoroalkene isosteres possessing a wide range of side chain functionalities.

Enantioselective synthesis of diverse α-amino phosphonate diesters

An efficient, versatile protocol for the synthesis of highly enantioenriched α-amino phosphonate diesters has been devised. Addition of lithium diethyl phosphite to chiral chelating imines 31a-j, prepared from a variety of aldehydes and the chiral auxilia

Diastereoselective addition of chiral aliphatic imines and 2-alkyl-1,3-oxazolidines to organometallic reagents

The reaction of organocerium reagents with chiral aliphatic imines derived from (R)-O-methylphenylglycinol afforded the corresponding amines with high diastereoselectivity. In contrast, the reaction of Grignard reagents with chiral 2-alkyl-1,3-oxazolidines derived from (R)-N-methylphenylglycinol afforded the amines with changeover in diastereoselectivity.