An "anti-Baldwin" 3-exo-dig cyclization: Preparation of vinylidene cyclopropanes from electron-poor alkenes

作者：Campbell Matthew J; Pohlhaus Patrick D; Min Geanna; Ohmatsu Kohsuke; Johnson Jeffrey S^*

来源：Journal of the American Chemical Society, 2008, 130(29): 9180-+.

DOI：10.1021/ja803553a

Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

• 出版日期2008-7-23