ASYMMETRIC SIMMONS-SMITH REACTIONS USING HOMOCHIRAL PROTECTING GROUPS

Article abstract of DOI:10.1016/S0040-4020(01)88107-2

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.