Catalytic Asymmetric Formation of δ‐Lactones by [4+2] Cycloaddition of Zwitterionic Dienolates Generated from α,β‐Unsaturated Acid Chlorides | Zendy

Tiseni Paolo S. | Zendy; Peters René | Zendy

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research