| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5283646 | Tetrahedron Letters | 2007 | 5 Pages |
Abstract
Addition reaction of two geometrical isomers of 1-chlorovinyl p-tolyl sulfoxides, derived from unsymmetrical ketones and chloromethyl p-tolyl sulfoxide, with lithium enolate of tert-butyl acetate gave single isomers of the adduct, respectively. Treatment of each diastereomer with i-PrMgCl resulted in the formation of magnesium carbenoids. Highly regiospecific 1,3-CH insertion reaction was found to take place from the magnesium carbenoids to afford cyclopropanes in high yields. Stereochemistry of the adducts, reaction mechanism, and origin of the regiospecificity are discussed.
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Authors
Shingo Ogata, Shigeyuki Masaoka, Ken Sakai, Tsuyoshi Satoh,