Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe
- Davies, Stephen G.
- Fletcher, Ai M.
- Hermann, Gesine J.
- Poce, Giovanna
- Roberts, Paul M.
- Smith, Andrew D.
- Sweet, Miles J.
- Thomson, James E.
- Smith, Andrew David
Publication date
July 2010
DOIAbstract
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.</p
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