A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids
The synthesis of alkylamino epoxides C is presented.Key steps include the synthesis of amino aldehyde 5 by reduction (DIBAH) of ester 3 or by oxidation of N-protected amino alcohol 4, both edducts of which are derived from amino acids.A study of the olefination of aldehyde 5 with unstabilized ylides is presented, and protected allylic amino 6, obtained in good to excellent optical purity, is oxidized (MCPBA) to epoxide C.Threo selectivity is observed in the epoxidation reaction.
Luly, Jay R.,Dellaria, Joseph F.,Plattner, Jacob J.,Soderquist, Jeffrey L.,Yi, Nwe
p. 1487 - 1492
(2007/10/02)
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