TY - JOUR A1 - Geddis, Stephen M. A1 - Hagerman, Caroline E. A1 - Galloway, Warren R. J. D. A1 - Sore, Hannah F. A1 - Goodman, Jonathan M. A1 - Spring, David R. T1 - (Z)-Selective Takai olefination of salicylaldehydes JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 323 EP - 328 SN - 1860-5397 DO - 10.3762/bjoc.13.35 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.35 KW - alkenyl iodides KW - salicylaldehydes KW - stereoselectivity KW - Takai olefination KW - transition state N2 - The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of salicylaldehyde derivatives. Systematic screening of related substrates led to the identification of key factors responsible for this surprising inversion of selectivity, and enabled the development of a modified mechanistic model to rationalise these observations. ER -