110919-08-9Relevant academic research and scientific papers
ASYMMETRIC SIMMONS-SMITH REACTIONS USING HOMOCHIRAL PROTECTING GROUPS
Mori, Atsunori,Arai, Isao,Yamamoto, Hisashi,Nakai, Hisao,Arai, Yoshinobu
, p. 6447 - 6458 (2007/10/02)
Asymmetric Simmons-Smith reactions of α,β-unsaturated acetals derived from chiral dialkyl tartrate or (2R,4R)-2,4-pentanediol are described.Treatment of the acetal with diethylzinc and methylene iodide gives a cyclopropane with high diastereoselectivity.The acetal group is readily transformed to the aldehyde or the ester group.In addition, the method is successfully applied to the enantioselective synthesis of 5,6-methanoleukotriene A4, a stable and selective inhibitor of leukotriene biosynthesis.
