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I – ‐Catalyzed Reaction of 5‐Methoxyoxazoles with Organic Iodides – An Efficient Synthesis of Azalactones
Author(s) -
Lu Lianghua,
Lu Ping,
Ma Shengming
Publication year - 2007
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.200600637
Subject(s) - chemistry , catalysis , alkyl , quaternary carbon , cleavage (geology) , medicinal chemistry , bond cleavage , oxygen , carbon fibers , organic chemistry , enantioselective synthesis , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
An I – ‐catalyzed methoxy carbon–oxygen bond cleavage in 5‐methoxyoxazoles leading to the synthesis of azalactones, precursors of quaternary amino acids, has been developed. A series of 4‐substituted azalactones were obtained through the variation of the alkyl iodides and differently substituted 5‐methoxyoxazoles. Further study indicated that azalactone 3aa may be easily converted to benzoyl‐protected quaternary amino acid 4aa . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)