111138-88-6

Upstream product

• 111060-82-3 (1R,2S)-2-(dibenzylamino)-1,3-diphenylpropan-1-ol 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 133316-59-3 benzostabase of Phe-OMe 
• 591-51-5 phenyllithium 
• 120238-42-8 methyl (S)-2-(diphenylmethylideneamino)-3-phenylpropanoate 
• 131472-77-0 2-(Benzhydrylidene-amino)-1,3-diphenyl-propan-1-ol 

Downstream Products

• 1016649-96-9 N₁,N₃-bis[(1R,2S)-1-hydroxy-1,3-diphenylpropan-2-yl]isophthalamide 
• 925672-29-3 C₃₀H₃₇NO₂ 

Relevant academic research and scientific papers

Vanadium-catalyzed asymmetric oxidation of sulfides using Schiff base ligands derived from ss-amino alcohols with two stereogenic centers

Novel Schiff base ligands derived from ss-amino alcohols with two stereogenic centers were prepared and. used in the preparation of optically pure sulfoxides by using aqueous hydrogen peroxide as the oxidant. A variety of sulfides were smoothly converted into the corresponding sulfoxides cata-lyzed by the chiral vanadium-Schiff base complex. Good yields (>80%) with excellent: enantioselectivities (>99%ee) were obtained in most cases.

The "benzostabase" protecting group for primary amines; application to aliphatic amines

The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control".

β-Amino alcohols from amino acids: Chelation control via Schiff bases

Sequential addition of iBu2AlH and RLi or RMgX to Schiff base esters derived from amino acids provides a simple route to β-amino alcohols. The reaction procedes without racemization, and with high threo selectivity. Several representative sphingosines are synthesized.

Synthesis and Stereoselective Reactions of 2-(Pyrrol-1-yl)alkanals and 2-(pyrrol-1-yl)alkan-1-ones

2-(2,5-Dimethylpyrrol-1-yl)alkanals, 2-(pyrrol-1-yl)alkanals, and 2-(2,5-dimethylpyrrol-1-yl)alkan-1-ones were prepared.The reactions of these compounds with Grignard and hydride reagents proceeded stereoselectively to give the corresponding 2-(pyrrol-1-yl)alcohols, which were converted into 2-aminoalcohols, such as norephedrine and ephedrine, by cleavage of the pyrrole ring.