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Regioselective and Diastereoselective Borono-Mannich Reactions with Pinacol Allenylboronate

Thanaphat Thaima and Stephen G. Pyne*

*School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia, Email:

T. Thaima, S. G. Pyne, Org. Lett., 2015, 17, 778-781.

DOI: 10.1021/ol503424k

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Borono-Mannich reactions of pinacol allenylboronate with salicylaldehyde and amines are highly regioselective and give homopropargylamine for secondary amines and α-allenylamine products for primary amines, respectively. In contrast, glycoaldehyde and chiral α-hydroxyaldehydes give exclusively anti-β-amino-β-allenyl alcohol products, irrespective of the nature of the amine component.

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Key Words

Petatis Reaction, allenes

ID: J54-Y2015