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Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation

✍ Scribed by Zhuqing Liu; C.Scott Shultz; Candice A. Sherwood; Shane Krska; Peter G. Dormer; Richard Desmond; Claire Lee; Edward C. Sherer; Joseph Shpungin; James Cuff; Feng Xu


Book ID
104098915
Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
456 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis


An efficient preparation of highly enantiomerically enriched aryl b-hydroxy a-amino esters via dynamic kinetic resolution (DKR), asymmetric transfer hydrogenation of a-amino b-keto esters is described. The anti b-hydroxyl a-amino esters were obtained both in high yields and high diasteroselectivity. The observed high anti selectivity is inconsistent with the previous results in literature. The absolute stereochemistry of the aryl b-hydroxy a-amino esters was unambiguously confirmed via chemical derivatization as well as Vibrational Circular Dichroism (VCD) techniques.


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