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- Title
Highly Stereoselective aza-Baylis-Hillman Reactions of CF<sub>3</sub>-Sulfinylimines: Straightforward Access to α-Methylene β-CF<sub>3</sub> β-Amino Acids.
- Authors
Milcent, Thierry; Hao, Jing; Kawada, Kosuke; Soloshonok, Vadim A.; Ongeri, Sandrine; Crousse, Benoit
- Abstract
1,4-Diazabicyclo[2.2.2]octane-catalyzed asymmetric aza-Baylis-Hillman (ABH) reaction of ( R)- N- tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine with various Michael acceptors proceeds with exceptionally high rates and stereochemical outcome. This ABH approach provides convenient and practical access to previously unknown enantiomerically pure α-methylene β-CF3 β-amino esters/acids, forthright useable for peptide synthesis.
- Subjects
STEREOSELECTIVE reactions; STEREOCHEMISTRY; BAYLIS-Hillman reaction; CARBON compounds; CARBENES
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 15, p3072
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402078