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Cyclopeptoids as Phase‐Transfer Catalysts for the Enantioselective Synthesis of α‐Amino Acids
Author(s) -
Schettini Rosaria,
Nardone Brunello,
De Riccardis Francesco,
Della Sala Giorgio,
Izzo Irene
Publication year - 2014
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.201403224
Subject(s) - enantioselective synthesis , chemistry , glycine , catalysis , alkylation , amino acid , proline , phase (matter) , stereochemistry , organic chemistry , combinatorial chemistry , biochemistry
The first application of cyclopeptoids in asymmetric phase‐transfer catalysis was examined. A small library of nine alternating N ‐substituted‐glycine and proline hexacyclopeptoids was tested in the enantioselective alkylation of N ‐(diphenylmethylene)glycine tert ‐butyl ester. The presence of an N ‐arylmethyl side chain in the catalyst was found to be crucial for the synthesis of α‐amino acids with up to 73 % ee .