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- Title
A Mild and Efficient CH<sub>2</sub>-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases.
- Authors
Pujari, Sandip A.; Besnard, Céline; Bürgi, Thomas; Lacour, Jérôme
- 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.
- Subjects
METHYLENE group; CHEMICAL reactions; CRYSTAL structure; STEREOCHEMISTRY; TROGER'S base; NITROGEN; CARBON; CHEMICAL synthesis
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 26, p7630
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201500435