Open AccessSynthesis of Enantiopure Triols from Racemic Baylis–Hillman Adducts Using a Diastereoselective Peroxidation Reaction
Author(s) -
Dylan S. Zuckerman,
K. A. Woerpel
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03439
Subject(s) - enantiopure drug , chemistry , adduct , baylis–hillman reaction , organic chemistry , stereoselectivity , stereochemistry , stereoisomerism , molecule , enantioselective synthesis , catalysis
Using a chiral (-)-menthone auxiliary, enantiopure cyclic derivatives of Baylis-Hillman adducts were synthesized. A diastereoselective peroxidation reaction was used to introduce an oxygen atom and establish another stereocenter. The resulting products could be elaborated by employing a one-flask reduction-acetylation protocol followed by a diastereoselective nucleophilic substitution reaction. Removal of the (-)-menthone auxiliary provided an enantiopure triol with a structure related to naturally occurring polyols.