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Air‐Stable Bifunctional Allylation Reagents for the Asymmetric Synthesis of Differentiated syn ‐ and anti ‐1,3‐Diols
Author(s) -
Lee Jae Seung,
Kim Dongeun,
Kong Suk Bin,
Han Hyunsoo
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204148
Subject(s) - bifunctional , enantioselective synthesis , chemistry , allylic rearrangement , aldehyde , reagent , diol , stereochemistry , organic chemistry , catalysis
Turning the diols : Enantiomerically pure bifunctional reagents I and ent ‐ I undergo asymmetric aldehyde allylation followed by Ir I ‐catalyzed enantioselective decarboxylative allylic etherification to give differentiated syn ‐ and anti ‐1,3‐diols with complete control of the absolute and relative stereochemistry (see scheme; PMP= para ‐methoxyphenyl, dbcot=dibenzo[ a , e ]cyclooctatetraene, DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene).