Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of L-α-Amino Aldehydes

Authors

Farzad Zamani, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

115386

Publication Details

Zamani, F., Pyne, S. G. & Hyland, C. J. T. (2017). Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of L-α-Amino Aldehydes. Journal of Organic Chemistry, 82 (13), 6819-6830.

Abstract

The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected L-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecting groups. A range of 1-allenyl-2-amino alcohols were obtained with excellent regioselectivity and converted to oxazolidinones and dihydrofurans. Many of which could be isolated as single diastereoisomers and without significant erosion of ee, making this a practical catalytic synthesis of highly functionalized heterocycles.