87837-32-9

Upstream product

• 779-53-3 4-morpholinylacetophenone 
• 110-91-8 morpholine 
• 20780-54-5 (S)-styrene oxide 
• 4432-34-2 2-morpholino-1-phenylethanol 
• 93-56-1 phenylethane 1,2-diol 
• 70-11-1 α-bromoacetophenone 
• 7322-88-5 (S)-acetylmandelic acid 
• 17199-29-0 (S)-Mandelic acid 
• 469874-40-6 (S)-1-[O-(acetyl)mandelyl]morpholine 

Downstream Products

• 863204-01-7 (S)-N-methyl-1-phenyl-2-(morpholin-1-yl)ethanamine 

Relevant academic research and scientific papers

An efficient synthesis of chiral nonracemic diamines: Application in asymmetric synthesis

A variety of chiral diamines have been synthesized from optically active mandelic acid in an efficient manner. The chiral nonracemic lithium amide base derived from one of the diamines has been used in formal asymmetric synthesis of natural products such as (-)-utenone A and (-)-carbovir.

Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -

Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.

Acid-Assisted Ru-Catalyzed Enantioselective Amination of 1,2-Diols through Borrowing Hydrogen

Here, we present a highly enantioselective synthesis of 1,2-amino alcohols from readily available racemic 1,2-diols through a borrowing hydrogen process. An intriguing acid effect was discovered for this Ru-catalyzed amination reaction, which led to a sig

Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions

The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.

Magnetic nano Fe3O4 catalyzed solvent-free stereo- and regioselective a-aminolysis of epoxides by amines; A green method for the synthesis of β-amino alcohols

We report the use of magnetic nano Fe3O4 as a mild heterogeneous catalyst for the aminolysis of epoxides with amines. The approach constitutes a green method for the formation of a variety of β-amino alcohols with very high stereo- and regioselectivity under solvent-free and ambient reaction conditions. The aminolysis of chiral epoxides with amines gave the corresponding chiral β-amino alcohols with complete inversion of stereochemistry. The magnetic nano Fe3O4 catalyst can be easily recovered and recycled. Georg Thieme Verlag Stuttgart New York.

Ruthenium-catalyzed enantioselective synthesis of β-amino alcohols from 1,2-diols by "borrowing hydrogen"

Enantioselective synthesis of β-amino alcohols from 1,2-diols by the use of [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS catalysis was developed. Several 1,2-diols were treated with secondary amines to afford the corresponding optically active

Application of tethered ruthenium catalysts to asymmetric hydrogenation of ketones, and the selective hydrogenation of aldehydes

An improved method for the synthesis of tethered ruthenium(II) complexes of monosulfonylated diamines is described, together with their application to the hydrogenation of ketones and aldehydes. The complexes were applied directly, in their chloride form, to asymmetric ketone hydrogenation, to give products in excess of 99% ee in the best cases, using 30 bar of hydrogen at 60 °C, and to the selective reduction of aldehydes over other functional groups. Copyright

Application of tethered ruthenium catalysts to asymmetric hydrogenation of ketones, and the selective hydrogenation of aldehydes

An improved method for the synthesis of tethered ruthenium(II) complexes of monosulfonylated diamines is described, together with their application to the hydrogenation of ketones and aldehydes. The complexes were applied directly, in their chloride form, to asymmetric ketone hydrogenation, to give products in excess of 99% ee in the best cases, using 30 bar of hydrogen at 60 °C, and to the selective reduction of aldehydes over other functional groups. Copyright

Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: Application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides. The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product.