112018-58-3

Upstream product

• 110811-22-8 O-benzyloxycarbonyl-N-(R)-(1-phenylethyl)-(S)-mandelamide 
• 110901-05-8 O-benzyloxycarbonyl-(S)-(+)-mandelic acid 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 78146-52-8 phenylglyoxal monohydrate 
• 7322-88-5 (S)-acetylmandelic acid 
• 17199-29-0 (S)-Mandelic acid 
• 469874-42-8 (S)(+)-N-[(R)-α-methylbenzyl]-O-acetyl mandelamide 
• 76353-13-4 (S)-N-<(R)-1-phenylethyl>mandelamine 
• 110811-21-7 1-Phenyl-2-[(E)-(R)-1-phenyl-ethylimino]-ethanone 

Relevant academic research and scientific papers

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.

The Preparation and Absolute Configuration of the Optically Active Forms of the Diastereoisomers of 2-(1-Phenylethyl)amino-1-phenylethanol and Their Use as Chiral Auxiliaries in the Asymmetric Reduction of Acetophenone with Modified Lithium Aluminium Hydrides

(1S,2S)-(-)-2-(1-Phenylethyl)amino-1-phenylethanol (4b) (α-form) and the (1S,2R)-(+)-diastereoisomer (4f) (β-form) were prepared by lithium aluminium hydride reduction of the optically active amides derived from the appropriate mandelic acids and 1-phenylethylamines.The preparative methods give the absolute stereochemistry.The aminoethanols (4) were used along with the lower alcohols to prepare chirally modified lithium aluminium hydrides which were in turn used to reduce acetophenone.The optical yields varied, giving at best, under low temperature conditions and use of a 25 percent optical yield.