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Synthesis of 1,2‐Diols and Their Base‐Initiated Rearrangement to Butyrolactones
Author(s) -
Moliterno Mauro,
Margarita Cristiana,
Panarello Silvia,
Salvio Riccardo,
Bella Marco
Publication year - 2014
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.201402853
Subject(s) - chemistry , dichloromethane , propargyl , aldol reaction , base (topology) , methanol , carroll rearrangement , alkyl , medicinal chemistry , organic chemistry , sigmatropic reaction , catalysis , solvent , mathematical analysis , mathematics
1,2‐Diols 3 have been synthesized by the aldol addition of hydroxy esters 1 to propargyl aldehydes 2 in dichloromethane. These 1,2‐diols undergo a base‐initiated rearrangement under mild conditions in methanol with an unusual 1,2‐alkyl shift to afford interesting α,β‐unsaturated γ‐butyrolactones 4 . A possible mechanism is postulated on the basis of experimental evidence and the results of DFT calculations.