Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction

G Bartoli, E Marcantoni, M Petrini

Index: Bartoli, Giuseppe; Marcantoni, Enrico; Petrini, Marino Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5834 - 5840

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Citation Number: 22

Abstract

Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF,-70" C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, ...