American Chemical Society
jo6b02765_si_001.pdf (4.35 MB)

A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2‑Amino-2-vinyl-1,3-diols

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journal contribution
posted on 2017-01-13, 00:00 authored by Aleix Rodríguez, Xavier Ariza, Miguel A. Contreras, Jordi Garcia, Paul Lloyd-Williams, Nerea Mercadal, Carolina Sánchez
Treatment of readily available allene 1 with Cy2BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected.