291313-74-1

Upstream product

• 591-51-5 phenyllithium 
• 291313-82-1 (4S,5S)-4-(hydroxymethyl)-4-methyl-5-phenyl-3-oxazolidin-2-one 
• 291313-73-0 (1S,7aS)-1-phenyl-5,5,7a-trimethyl-2,6-dioxa-4-azapentalen-3-one 
• 291313-71-8 (S)-N-(tert-butoxycarbonyl)-4-[(R)-1'-phenylcarbinol]-2,2,4-trimethyl-3-oxazolidine 
• 1130164-74-7 (2R,3S)-2-amino-2-methyl-3-pivaloyloxy-3-phenylpropanoic acid 
• 1130164-75-8 (2R,3S)-2-methyl-2-pivaloylamino-3-benzyloxycarbonyloxy-3-phenylpropanoic acid 
• 338-69-2 D-Alanine 
• 100-52-7 benzaldehyde 

Downstream Products

• 81132-49-2 methyl (2R,3S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoate 
• 302-72-7 rac-Ala-OH 

Relevant academic research and scientific papers

Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids

We report the synthesis of diverse β-hydroxy-α,α-dialkyl-α-amino acids with perfect stereoselectivity for the α-quaternary center through the action of l- and d-specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80 % were obtained. In the case of d-selective threonine aldolase from Pseudomonas sp., generally higher diastereoselectivities were observed. The applicability of the protocol was demonstrated by performing enzymatic reactions on preparative scale. Using the d-threonine aldolase from Pseudomonas sp., (2R,3S)-2-amino-3-(2-fluorophenyl)-3-hydroxy-2-methylpropanoic acid was generated in preparative amounts in one step with a diastereomeric ratio >100 favoring the syn-product. A Birch-type reduction enabled the reductive removal of the β-hydroxy group from (2S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid to generate enantiopure l-α-methyl-phenylalanine via a two-step chemo-enzymatic transformation.

Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3- pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: Asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3- phenylpropanoic acid

Treatment of a range of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3- oxazolidin-5-ones with LDA followed by the addition of allyl bromide promotes highly stereoselective allylation (>98% de) at the 4-position of the oxazolidinone ring anti to the s

Asymmetric synthesis of all isomers of α-methyl-β-phenylserine

This report describes the synthesis of enantiomerically pure (2R,3R)-, (2R,3S)-, (2S,3S)- and (2S,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acids, four quaternary α-amino acids, using a stereodivergent synthetic route and starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals. The key step involves the asymmetric Grignard additions to the above chiral aldehydes, in which high levels of asymmetric induction are observed. Copyright (C) 2000 Elsevier Science Ltd.