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Title

A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases

Authors
Pujari, Sandip A.
Published in Angewandte Chemie: International Edition. 2015, vol. 54, no. 26, p. 7520-7523
Abstract A novel CH2-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 CH2 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.
Keywords Configuration determinationEnantioselectivityHeterocyclesRing contractionStereochemistry
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Other version: http://doi.wiley.com/10.1002/anie.201500435
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Research groups Groupe Bürgi
Groupe Lacour
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PUJARI, Sandip A. et al. A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases. In: Angewandte Chemie: International Edition, 2015, vol. 54, n° 26, p. 7520-7523. https://archive-ouverte.unige.ch/unige:73259

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Deposited on : 2015-06-19

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