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Shono‐Type Oxidation for Functionalization of N‐Heterocycles
Author(s) -
Yamamoto Kosuke,
Kuriyama Masami,
Onomura Osamu
Publication year - 2021
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.202100031
Subject(s) - chemistry , enantioselective synthesis , electrochemistry , cyclic amines , halogen , chirality (physics) , combinatorial chemistry , organic chemistry , organic synthesis , catalysis , electrode , nambu–jona lasinio model , quark , alkyl , chiral symmetry breaking , physics , quantum mechanics
The development of facile synthetic methods for stereodefined aliphatic cyclic amines is an important research field in synthetic organic chemistry since such scaffolds constitute a variety of natural products and biologically active compounds. N ‐Acyl cyclic N , O ‐acetals which prepared by electrochemical oxidation of the corresponding cyclic amines have proven to be useful and versatile precursors for the synthesis of such skeletons. In this Personal Account , we introduce our efforts toward the development of synthetic strategies for the diastereo‐ and/or enantioselective synthesis of cyclic amines by using electrochemically prepared cyclic N , O ‐acetals. In addition, the investigation of the “memory of chirality” in the electrooxidative methoxylation of N ‐acyl amino acid derivatives, the strategy for the synthesis of chiral azabicyclic compounds by utilizing electrochemical oxidation, and halogen cation‐mediated synthesis of nitrogen‐containing heterocycles are also described.