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

Journal Article


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.

Publication Date


  • 2017

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85022341288

Number Of Pages


  • 11

Start Page


  • 6819

End Page


  • 6830

Volume


  • 82

Issue


  • 13

Place Of Publication


  • United States

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.

Publication Date


  • 2017

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85022341288

Number Of Pages


  • 11

Start Page


  • 6819

End Page


  • 6830

Volume


  • 82

Issue


  • 13

Place Of Publication


  • United States