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A Versatile Route to syn‐ and anti ‐α‐Amino β‐Hydroxy Esters from β‐Keto Esters by Dynamic Kinetic Resolution with Ru‐SYNPHOS ® Catalyst
Author(s) -
Mordant Céline,
Dünkelmann Pascal,
RatovelomananaVidal Virginie,
Genet JeanPierre
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400078
Subject(s) - chemistry , kinetic resolution , catalysis , hydrochloride , amino esters , selectivity , organic chemistry , amino acid , combinatorial chemistry , enantioselective synthesis , biochemistry
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 Ru II ‐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)