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Efficient Synthesis of cis ‐3‐Substituted Prolines by Bidentate‐Assisted Palladium Catalysis
Author(s) -
Feng Ruokun,
Wang Binjie,
Liu Yue,
Liu Zhanxiang,
Zhang Yuhong
Publication year - 2015
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.201403191
Subject(s) - chemistry , alkylation , palladium , catalysis , denticity , combinatorial chemistry , surface modification , functional group , stereochemistry , proline , amino acid , organic chemistry , metal , biochemistry , polymer
A highly effective protocol for the synthesis of C‐3‐substituted prolines has been developed. Pd‐catalyzed C(sp 3 )–H activation is used for the straightforward functionalization of prolines. The use of an 8‐aminoquinolinecarboxamide directing group allows direct arylation, alkenylation, and alkylation at the C‐3 position of prolines in moderate to high yields with diverse iodo‐ or bromo precursors. The resulting 3‐substituted proline derivatives are important units in many biologically active compounds and are useful promoters for a variety of functional group transformations.