A Mild and Efficient CH 2 ‐Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases | Zendy

Pujari Sandip A. | Zendy; Besnard Céline | Zendy; Bürgi Thomas | Zendy; Lacour Jérôme | Zendy

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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.

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