Synthesis of highly epimerizable N-protected [alpha]-amino aldehydes of high enantiomeric excess

Myers, A.G., Zhong, B., Movassaghi, M., Kung, D.W., Lanman, B.A., Kwon, S. (2000)

Tetrahedron Letters, 41(9), 1359-1362

The Dess–Martin periodinane was found to be a superior oxidant for the efficient, epimerization-free synthesis of optically active N-protected [alpha]-amino aldehydes from the corresponding N-protected [alpha]-amino alcohols. Highly racemization-prone products, including N-Fmoc phenylglycinal and N-trifluoroacetyl 9alpha]-amino aldehydes, were prepared in >95% yield with <1% epimerization.

Subject Headings: Amino aldehydes; High enantiomeric excess; Epimerizable

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Type: Journal Article

Serial number: 2542