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Organocatalytic Enantioselective Michael–Henry Acetalization of Glutaraldehyde and 3‐Aryl‐2‐nitroprop‐2‐enols: A Facile Entry to 3‐Oxabicyclo[3.3.1]nonan‐2‐ones with Four Consecutive Stereogenic Centers
Author(s) -
Hong BorCherng,
Lan DingJyun,
Dange Nitin S.,
Lee GeneHsiang,
Liao JuHsiou
Publication year - 2013
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.201201496
Subject(s) - stereocenter , enantioselective synthesis , chemistry , michael reaction , organocatalysis , glutaraldehyde , aryl , stereochemistry , catalysis , organic chemistry , alkyl
A convenient method was developed for the enantioselective (>99 % ee ) synthesis of 3‐oxabicyclo[3.3.1]nonan‐2‐ones containing four consecutive stereogenic centers. The method comprises a cascade organocatalytic Michael–Henry acetalization–oxidation reaction of glutaraldehyde and 3‐aryl‐2‐nitroprop‐2‐enols. The structures and absolute configurations of the products were confirmed by X‐ray analysis.