Addition of gamma-silyloxyallyltins on ethyl glyoxylate: evaluation of the influence of the experimental conditions on the stereochemical course of the reaction

作者：Lumbroso Alexandre; Kwiatkowski Piotr; Blonska Anna; Le Grognec Erwan; Beaudet Isabelle; Jurczak Janusz^*; Jarosz Slawomir; Quintard Jean Paul

来源：Tetrahedron, 2010, 66(8): 1570-1580.

DOI：10.1016/j.tet.2009.12.037

• gamma-Silyloxyallyltributyltins
• Ethyl glyoxylate
• Allylstannation
• Diastereoselective synthesis
• Reaction mechanisms

Ethyl glyoxylate was reacted with alpha-substituted gamma-(t-butyldimethylsilyloxy)-allyltributyltin in order to obtain selectively each diastereomer of ethyl 3-(t-butyldimethylsilyloxy)-2-hydroxyhex-4-enoate and subsequently the corresponding diols. Diastereomers syn-E, anti-E and anti-Z were obtained in good yields with good to high selectivities and the obtained results were rationalized by consideration of cyclic or open transition states in agreement with the experimental conditions and with the structure of the starting reagents.

• 出版日期2010-2-20