Stereochemistry of addition of allylic Grignard reagents to 3-(hydroxymethyl) cyclopropenes
HG Richey Jr, RM Bension
Index: Richey, Herman G.; Bension, Rouvain M. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5036 - 5042
Full Text: HTML
Citation Number: 36
Abstract
Allylic Grignard reagents add to the double bonds of alkyl-substituted 3-(hydroxymethy1) cyclopropenes. In the products, both the allyl group and the group (H or C02H) 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.
Related Articles:
2-Acetoxybenzoyl Bromide, a Convinient Reagent for the Synthesis of Oxiranes from vic-Diols
[Bhat, K. S.; Joshi, P. L.; Rao, A. S. Synthesis, 1984 , # 2 p. 142 - 145]
[Chahdoura, Faouzi; Pradel, Christian; Gomez, Montserrat Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3648 - 3660]
[Chahdoura, Faouzi; Pradel, Christian; Gomez, Montserrat Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3648 - 3660]
[Nishiyama, Hisao; Matsumoto, Makoto; Arai, Hiroyuki; Sakaguchi, Hisao; Itoh, Kenji Tetrahedron Letters, 1986 , vol. 27, # 14 p. 1599 - 1602]
New chemical cross-coupling between aryl halides and allylic acetates using a cobalt catalyst
[Organic Letters, , vol. 5, # 7 p. 1043 - 1045]