550-58-3

Upstream product

• 39664-88-5 N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]formamide 
• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 813459-63-1 ((1S,2R)-2-Hydroxy-1,2-diphenyl-ethyl)-carbamic acid methyl ester 
• 301191-47-9 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]formamide 
• 1380213-66-0 C₄₇H₅₉ClN₄O₆SSi 
• 186581-53-3 diazomethane 
• 134-81-6 benzil 
• 74-89-5 methylamine 
• 64-17-5 ethanol 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 74-88-4 methyl iodide 
• 39664-86-3 (+/-)-N-(erythro-α'-hydroxy-bibenzyl-α-yl)-formamide 
• 54852-85-6 N-methylamino-2 diphenyl-1,2 ethanol 

Downstream Products

• 46864-14-6 (1S,2R)-N,N-dimethyl-2-hydroxy-1,2-diphenyl-ethylamine 
• 156592-83-5 (1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol 
• 1279115-36-4 C₁₅H₁₆N₂O₂ 
• 1279115-26-2 (1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol 
• 1279115-37-5 C₁₅H₁₆N₂O₂ 
• 1279115-31-9 (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol fumarate 
• 1279115-30-8 (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol 
• 1380325-25-6 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methylbutyramide 
• 1380325-29-0 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methyl-2-methylenebutanamide 
• 1380325-30-3 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methyl-2-methyleneheptanamide 
• 1380325-28-9 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methylhexanamide 
• 1380325-31-4 (R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide 
• 1380325-33-6 CF₃O₃S^(1-)*C₂₅H₂₆NO⁽¹⁺⁾ 
• 1380325-34-7 (R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylhexanamide 

Relevant academic research and scientific papers

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones

We report an unprecedented organocatalytic enantioselective acyloin rearrangement of α,α-disubstituted α-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, α-hydroxy acetals rearranged to α-alkoxy ketones in good to high yields with high enantioselectivities. Formation of an ion pair between the in situ generated oxocarbenium ion and the chiral phosphoramide anion was proposed to be responsible for the highly efficient transfer of chirality. Conditions for removal of cyclohexyl and cyclopentyl groups from the corresponding α-alkoxy ketones were uncovered underpinning their potential general utility as hydroxy protecting groups. Conversion of the rearranged products to the enantioenriched α-hydroxy ketone, 1,2-diol, β-amino alcohol and 1,4-dioxane was also documented.

Collective Synthesis of cladiellins based on the gold-catalyzed cascade reaction of 1,7-diynes

The cladiellin family of natural products, which includes molecules with various biological activities, continues to invite new synthetic studies. A gold-catalyzed tandem reaction of 1,7-diynes to construct the 6-5-bicyclic ring systems that are present in a number of natural products was developed. This reaction was applied as the key step to realize the formal and total syntheses of nine members of the cladiellin family in an enantio- and diastereoselective manner. This modular and efficient approach could also be used for the construction of other cladiellins, as well as their analogues, for follow-up studies. Clad(iellins) in gold: A gold-catalyzed tandem reaction of 1,7-diynes was previously developed to construct the 6-5-bicyclic ring systems that are present in a number of natural products. This reaction was applied to realize the total synthesis of nine members of the cladiellin family. This modular and efficient approach, which is enantio- and stereoselective, could also be used for the construction of other cladiellins and their analogues. Copyright

A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine

A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivat

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.

Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis

Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright

A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of aspidosperma alkaloids

Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The intermediate is prepared in one step from the shown lactam through an electrophilic double-cyclization cascade (see scheme; Tf= trifluoromethanesulfonyl). Copyright

Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lith

Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation

Palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to

Aminophosphine phosphinites derived from chiral 1,2-diphenyl-2-aminoethanols: Synthesis and application in rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives

A series of chiral aminophosphine phosphinites DPAMPPs was synthesized from optically active 1,2-diphenyl-2-aminoethanols. The erythro-DPAMPPs were found to serve as excellent ligands for rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives. For an array of dehydroamino acid precursors, remarkably high enantioselectivity (up to 98.4% e.e.) and reactivity (the ratio of substrate/catalyst up to 10000) were observed. Some factors controlling the enantioselectivity were examined and discussed. (C) 2000 Elsevier Science Ltd.