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Asymmetric Desymmetrization of the Diallyl Acetals of Alkynals by the Enantioselective Pauson–Khand‐Type Reaction Catalysts
Author(s) -
Kim Dong Eun,
Lee Bo Hyung,
Rajagopalasarma Mudigonda,
Genêt JeanPierre,
RatovelomananaVidal Virginie,
Jeong Nakcheol
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800514
Subject(s) - desymmetrization , chemistry , enantioselective synthesis , diastereomer , catalysis , enantiomer , hydrolysis , organic chemistry , pauson–khand reaction , medicinal chemistry , stereochemistry
Asymmetric desymmetrization of the diallyl acetals of alkynal ( 1 ) by an enantioselective Pauson–Khand‐type reaction catalyst was studied. The corresponding 5‐oxabicyclo[3.3.0]octenones ( 2 ) were obtained as a mixture of diastereomers ( 2a and 2b ), which were hydrolyzed to afford a single enantiomer ( 3 ), in high yields (up to 88%) as well as excellent enantioselectivities (up to 97%).