Generation and Conjugate Additions of o‐Quinone Methides Under Mild Base Conditions: Rapid Synthesis of N‐Substituted Aryl Glycine Derivatives. Issue 36 (19th November 2013)

• Record Type: Journal Article
• Authors: Wang, Wei; Zheng, Zhong; Wang, Xiangmin; Chen, Jinchun
• Is Part Of: European journal of organic chemistry. Issue 36(2013)
• Page Start: 8299
• Page End: 8306
• Publication Date: 2013-11-19
• Subjects: Domino reactions -- Michael addition -- Reactive intermediates -- Amines -- Amino acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301018
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : A one‐step cascade approach was observed to give N ‐substituted aryl glycine derivatives from ( ortho ‐hydroxymethyl)aryl benzoates under very mild conditions. The proposed mechanism involves the generation of an ortho ‐quinone methide and its in situ conjugate addition. Various substituent groups on the substrate and different amines as the nucleophile were investigated.