Stereocontrolled Synthesis of (E)-Olefin Dipeptide Isosteres using a [3,3] Allylic Trichloracetimidate Rearrangement

Abstract
The addition of Z-vinylic cuprates to enantiopure α-alkyl β-alkoxy aldehydes afforded syn allylic monoprotected diols in high diastereomerical purity. The sigmatropic rearrangement of trichloracetimidates derived from these monoprotected diols afforded protected allylic aminoalcohols which were oxidized into E-Alkene dipeptide isosteres.

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