Journal of Organic Chemistry p. 1487 - 1492 (1987)
Update date:2022-07-29
Topics: Synthesis Epoxide Chemical Reaction Protected Experimental α-amino acids
Luly, Jay R.
Dellaria, Joseph F.
Plattner, Jacob J.
Soderquist, Jeffrey L.
Yi, Nwe
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.
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