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Facile Diastereoselective Synthesis of 2,6‐Dialkyl‐5‐methylene‐1,3‐dioxan‐4‐ones via α‐Activated Vinyl Esters
Author(s) -
Drewes Siegfried E.,
Emslie Neville D.,
Karodia Nazira,
Khan Abdullah A.
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230641
Subject(s) - chemistry , dabco , intramolecular force , diastereomer , methylene , aldehyde , transesterification , nucleophile , nucleophilic addition , molecule , medicinal chemistry , organic chemistry , octane , methanol , catalysis
Vinyl esters such as 2, in the presence of DABCO, undergo intial reaction with aldehydes, followed by nucleophilic attack on a second aldehyde molecule. Subsequent intramolecular transesterification affords the dioxanones 5 in high yields and high diastereomeric excesses.