Chromium-Mediated Stereoselective Synthesis of Carbohydrate-Derived (E)-alpha,beta-Unsaturated Esters or Amides

作者:Rodriguez Solla Humberto*; Concellon Carmen; Blanco Elena G; Sarmiento Juan Ignacio; Diaz Pamela; Soengas Raquel G
来源:Journal of Organic Chemistry, 2011, 76(13): 5461-5465.
DOI:10.1021/jo200548g

摘要

A chromium-mediated novel synthesis of carbohydrate-derived di- and trisubstituted (E)-alpha,beta-unsaturated esters or amides from a range of dichloroesters or amides and a variety of sugar aldehydes is reported. The process took place with total stereoselectivity and in high yields. A mechanism based on a sequential chromium-promoted aldol-type reaction and a completely stereoselective beta-elimination reaction is proposed to explain these results.

  • 出版日期2011-7-1