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Stereochemistry of Addition of Allylic Grignard Reagents to 3-(Hydroxymethyl)cyclopropenes
Richey, Herman G.,Bension, Rouvain M.
, p. 5036 - 5042 (1980)
Allylic Grignard reagents add to the double bonds of alkyl-substituted 3-(hydroxymethyl)cyclopropenes.In the products, both the allyl group and the group (H or CO2H) replacing magnesium are cis to the hydroxymethyl group.The new carbon-carbon bond is formed preferentially at the more substituted allylic carbon of the allyl group and at the more substituted carbon of the cyclopropene double bond.
