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A Mild and Efficient CH 2 ‐Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases
Author(s) -
Pujari Sandip A.,
Besnard Céline,
Bürgi Thomas,
Lacour Jérôme
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500435
Subject(s) - stereocenter , chemistry , bicyclic molecule , extrusion , stereochemistry , reactive extrusion , ring (chemistry) , organic chemistry , enantioselective synthesis , materials science , catalysis , polymer , metallurgy
A novel CH 2 ‐extrusion reaction leading to the transformation of ethano‐Tröger bases into disubstituted methano derivatives is reported (yields up to 93 %). Under mild and metal‐free oxidative conditions, a loss of CH 2 and a ring contraction are provoked. Despite two bond cleavages at stereogenic nitrogen and carbon centers and a temporary rupture of the bicyclic structure, a very high enantiospecificity (es≥98 %) is observed for this unusual reaction.