Three‐Component Sequential Aza[4+2] Cycloaddition/Allylboration/Retro‐Sulfinyl‐Ene Reaction: A New Stereocontrolled Entry to Palustrine Alkaloids and Other 2,6‐Disubstituted Piperidines | Zendy

Touré Barry B. | Zendy; Hall Dennis G. | Zendy

Premium

Three‐Component Sequential Aza[4+2] Cycloaddition/Allylboration/Retro‐Sulfinyl‐Ene Reaction: A New Stereocontrolled Entry to Palustrine Alkaloids and Other 2,6‐Disubstituted Piperidines

Author(s) -

Touré Barry B.,

Hall Dennis G.

Publication year - 2004

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.200353152

Subject(s) - component (thermodynamics) , ene reaction , cycloaddition , derivative (finance) , chemistry , stereochemistry , computer science , combinatorial chemistry , organic chemistry , catalysis , physics , financial economics , economics , thermodynamics

Step‐economy and stereocontrol are highlighted in a novel three‐component sequential reaction to access substituted piperidines (see scheme). Through combining boronate‐substituted hydrazonobutadienes, chiral sulfinimide dienophiles, and aldehydes in a highly regio‐ and diastereoselective fashion, a concise synthesis of the palustrine derivative (−)‐methyl dihydropalustramate was accomplished.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research