Premium
Catalytic Asymmetric Formation of δ‐Lactones by [4+2] Cycloaddition of Zwitterionic Dienolates Generated from α,β‐Unsaturated Acid Chlorides
Author(s) -
Tiseni Paolo S.,
Peters René
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200700859
Subject(s) - stereocenter , cycloaddition , chemistry , catalysis , silylation , aldehyde , amine gas treating , organic chemistry , enantioselective synthesis , medicinal chemistry
Smooth elaboration : Versatile δ‐lactone building blocks are provided by tertiary‐amine‐catalyzed asymmetric [4+2] cycloadditions of α,β‐unsaturated acid chlorides and the electron‐poor aldehyde chloral (see scheme). Silyl‐substituted acid chlorides (R 1 =R 3 Si) can be used for the diastereoselective synthesis of β‐hydroxy‐δ‐lactones possessing quaternary stereocenters.