Synthesis 2017; 49(13): 2913-2916
DOI: 10.1055/s-0036-1558967
special topic
© Georg Thieme Verlag Stuttgart · New York

E/Z-Selectivity Controlled by Participation of Internal Oxy Group During Electrophilic Substitution of Alk-1-enylboronate with Bis(2,4,6-trimethylpyridine)iodonium Salt

Morifumi Fujita*
Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan   Email: fuji@sci.u-hyogo.ac.jp
,
Hee Jin Lee
Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan   Email: fuji@sci.u-hyogo.ac.jp
,
Chisaki Ichihara
Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan   Email: fuji@sci.u-hyogo.ac.jp
,
Takashi Sugimura
Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan   Email: fuji@sci.u-hyogo.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 December 2016

Accepted after revision: 16 February 2017

Publication Date:
14 March 2017 (eFirst)

Abstract

Stereospecific inversion of configuration was observed in electrophilic iodo-substitution of 4-benzoyloxybut-1-enylboronate using bis(2,4,6-trimethylpyridine)iodine(I) salt, rationalized by participation of the internal benzoyloxy group.

Supporting Information

 
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