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Generation and Conjugate Additions of o ‐Quinone Methides Under Mild Base Conditions: Rapid Synthesis of N ‐Substituted Aryl Glycine Derivatives
Author(s) -
Wang Wei,
Zheng Zhong,
Wang Xiangmin,
Chen Jinchun
Publication year - 2013
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.201301018
Subject(s) - chemistry , nucleophile , benzoates , aryl , conjugate , hydroxymethyl , glycine , yield (engineering) , base (topology) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , amino acid , mathematical analysis , biochemistry , alkyl , materials science , mathematics , metallurgy
A one‐step approach was observed to give N ‐substituted aryl glycine derivatives in good to excellent yields (up to 93 %) from ( ortho ‐hydroxymethyl)aryl benzoates. A cascade mechanism was proposed for the generation and in situ conjugate addition of the ortho ‐quinone methides. This mechanism is strongly supported by our subsequent findings that tertiary amines could promote the process. Different functional groups on the ( ortho ‐hydroxymethyl)aryl benzoates and various amines were investigated to explore the scope of this cascade process. The substituents on the substrates strongly affected the reaction time and yield, and various primary and secondary amines were used as nucleophiles. The addition of tertiary amines enhanced the addition process for less basic nucleophiles.