Brad Sleebs - Diastereoselective synthesis highly functionalised β2,2,3-amino acids from 4-substituted-1,3-oxazinan-6-ones

Document created by Brad Sleebs on Aug 22, 2014
Version 1Show Document
  • View in full screen mode

  Publication Details (including relevant citation   information):

  Tetrahedron  (2012),   68(24),   4745-4756.

  Abstract:

  1,3-Oxazinan-6-ones were used to generate substituted   β2,2,3-substituted amino acid derivatives. The   enolates of 1,3-oxazinan-6-ones were trans-selectively   intercepted with electrophiles. This alkylation was subsequently   optimized for a one-pot dialkylation to form 5,5-disubstituted   oxazinanones. The initial 5-monomethylated compounds could be   enolized and then diastereoselectively intercepted with different   electrophiles to form differentially 5,5-disubstituted products.   The 5,5-dialkylated oxazinanones were then transformed to   N-methyl β2,2,3-substituted amino acids by   reductive cleavage. Hydrolysis or solvolysis of the oxazinanones   afforded β2,2,3-substituted amino acids or esters,   respectively. The chemistry thus provides access to a range of   symmetrical and stereopure β2,2,3-substituted amino   acids and further establishes 1,3-oxazinan-6-ones as useful   intermediates.

  Address (URL): http://dx.doi.org.ezp.lib.unimelb.edu.au/10.1016/j.tet.2012.04.012

 

Attachments

    Outcomes