4.4 Article

A highly efficient transformation of cis- to trans-cinnamic acid derivatives by iodine

Journal

TETRAHEDRON LETTERS
Volume 56, Issue 52, Pages 7197-7200

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.11.050

Keywords

Cinnamic acid derivative; Transformation; Iodine; Anti-diiodo intermediate

Funding

  1. National Natural Science Foundation of China [81460648, 81460536]
  2. Program for Changjiang Scholars and Innovative Research Team in University [IRT13095]

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Cinnamic acid derivatives (CAs), which have proven to be versatile components, are present in abundance in biologically active natural products, and are widely used as intermediates in the manufacture of pharmaceuticals, and chemicals. The presence of cis- and trans-CAs created difficulties for natural product and organic synthetic studies. A highly efficient method that utilized iodine to entirely convert cis- CAs into their trans-forms was developed to solve this problem. The mechanism of study revealed this conversion occurred via an anti-diiodo intermediate. (C) 2015 Elsevier Ltd. All rights reserved.

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