Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5278152 | Tetrahedron Letters | 2006 | 5 Pages |
Abstract
Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from various cyclic ketones and chloromethyl p-tolyl sulfoxide in three steps, in high yields, with lithium enolate of tert-butyl acetate or its homologues gave the adducts in quantitative yields. The adducts were treated with isopropylmagnesium chloride in ether in dry toluene as the reaction solvent to afford bicyclo[n.1.0]alkanes in high to quantitative yields via magnesium carbenoid 1,3-CH insertion. When this method was carried out starting from unsymmetrical cyclic ketones and (R)-chloromethyl p-tolyl sulfoxide, an asymmetric synthesis of bicyclo[n.1.0]alkane was realized.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Tsuyoshi Satoh, Shingo Ogata, Daisuke Wakasugi,