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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 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.201500435
Subject(s) - stereocenter , bicyclic molecule , extrusion , chemistry , stereochemistry , ring (chemistry) , reactive extrusion , contraction (grammar) , medicinal chemistry , organic chemistry , enantioselective synthesis , materials science , polymer , catalysis , metallurgy , medicine
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.