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DBU Catalysed Enantioselective Degradative Rearrangement: a Way to Tetrasubstituted 2‐Aryl‐2‐Amino Esters
Author(s) -
Loro Camilla,
Sala Roberto,
Penso Michele,
Foschi Francesca
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100493
Subject(s) - chemistry , enantioselective synthesis , aryl , catalysis , enantiomer , amino acid , enantiomeric excess , organic chemistry , combinatorial chemistry , alkyl , biochemistry
Herein we report a catalytic, easily scalable protocol for the enantioselective synthesis of Tetrasubstituted α‐aryl‐α‐amino acid derivatives, using a biphasic system composed by catalytic DBU in DME and aqueous solutions of Na 2 CO 3 . Under very mild reaction conditions, without using metal or chiral additives, this heterogeneous system promotes the degradative rearrangement of functionalized N ‐aryl sulphonyl α‐amino esters into the corresponding tetrasubstituted 2‐aryl‐2‐amino esters, with high enantiomeric ratios (up to 97.5:2.5) and good yields (up to 95%).