On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICI-NaOMe or ICI-pyridine

Lightfoot, A.P.; Twiddle, S.J.R.; Whiting, A.

Abstract

Conversion of hindered alkenyl boronate esters into the corresponding iodoalkene, or alkenyl chloride can be carried out stereoselectively using ICl. In the presence of NaOMe, direct reaction of ICl is favoured yielding the E-iodoalkene, however, the reaction with ICl followed by NaOMe can be used to give different major alkenyl iodide and chloride products, depending upon reaction temperature, ICl source and alkenyl boronate stereoelectronics. (C) 2004 Elsevier Ltd. All rights reserved.

Citation

Lightfoot, A., Twiddle, S., & Whiting, A. (2004). On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICI-NaOMe or ICI-pyridine. Tetrahedron Letters, 45(46), 8557-8561

• Journal Article Type: Article
• Publication Date: 2004-11
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 45
• Issue: 46
• Pages: 8557-8561
• Public URL: https://durham-repository.worktribe.com/output/1593442