Air‐Stable Bifunctional Allylation Reagents for the Asymmetric Synthesis of Differentiated  syn ‐ and  anti ‐1,3‐Diols | Zendy

Lee Jae Seung | Zendy; Kim Dongeun | Zendy; Kong Suk Bin | Zendy; Han Hyunsoo | Zendy

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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).

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