TY - JOUR
T1 - The first example of regiospecific magnesium carbenoid 1,3-CH insertion
T2 - its mechanism and stereochemistry
AU - Ogata, Shingo
AU - Masaoka, Shigeyuki
AU - Sakai, Ken
AU - Satoh, Tsuyoshi
PY - 2007/7/16
Y1 - 2007/7/16
N2 - 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.
AB - 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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U2 - 10.1016/j.tetlet.2007.05.101
DO - 10.1016/j.tetlet.2007.05.101
M3 - Article
AN - SCOPUS:34250315397
SN - 0040-4039
VL - 48
SP - 5017
EP - 5021
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 29
ER -