Journal of Organic Chemistry p. 1851 - 1855 (2017)
Update date:2022-08-11
Topics:
Rodríguez, Aleix
Ariza, Xavier
Contreras, Miguel A.
Garcia, Jordi
Lloyd-Williams, Paul
Mercadal, Nerea
Sánchez, Carolina
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.
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