A Versatile Route to syn‐ and anti‐α‐Amino β‐Hydroxy Esters from β‐Keto Esters by Dynamic Kinetic Resolution with Ru‐SYNPHOS® Catalyst
- 28 June 2004
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2004 (14) , 3017-3026
Abstract
A general and practical synthesis of both syn‐ and anti‐α‐amino β‐hydroxy esters with high levels of selectivity by the use of Ru‐SYNPHOS® catalysts is reported. The key transformations include asymmetric hydrogenations of α‐N‐substituted β‐keto esters protected as α‐amido or α‐amino hydrochloride derivatives, respectively. The RuII‐catalyzed hydrogenation of α‐amino β‐keto ester hydrochlorides affords the corresponding anti‐α‐amino β‐hydroxy esters with high diastereoselectivities (up to 99%) and enantioselectivities (up to 97%) through dynamic kinetic resolution (DKR). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)Keywords
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