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Organocatalytic Enantioselective 1,3‐Dipolar [6+4] Cycloadditions of Tropone
Author(s) -
Bertuzzi Giulio,
McLeod David,
Mohr LisaMarie,
Jørgensen Karl Anker
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003329
Subject(s) - tropone , decane , enantioselective synthesis , cycloaddition , chemistry , stereoselectivity , catalysis , series (stratigraphy) , computational chemistry , organic chemistry , paleontology , biology
A highly stereoselective 1,3‐dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2‐aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2‐aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee . A series of transformations, as well as a mechanistic proposal, are presented.