An efficient synthesis of cyclopropyl silyl ketones

作者：Honda Mitsunori^*; Nakae Kenta; Nishizawa Toshiaki; Suda Mitsuhiro; Kunimoto Ko Ki; Segi Masahito

来源：Tetrahedron, 2011, 67(49): 9500-9508.

DOI：10.1016/j.tet.2011.10.013

The reaction of silylcyclopropyl bromides with dichloromethyl methyl ether in the presence of n-butyllithium is investigated. Under basic reaction conditions, the corresponding cyclopropylidene derivatives are exclusively obtained. The resulting cyclopropylidene compounds are subjected to protonolysis or trapping with electrophiles in a one-pot to give the cyclopropyl silyl ketone derivatives in good yields. Acidic treatment of derived cyclopropyl silyl ketone allows isomerization to give the thermodynamically favorable trans form exclusively.

• 出版日期2011-12-9