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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.