Site and stereoselectivity of the cyclopropanation of unsymmetrically substituted 1,3-dienes by the Simmons-Smith reaction

Article abstract of DOI:10.1080/00397919608002620

In the Simmons-Smith reaction, 1,3-dienes are preferentially cyclopropanated at the more electron-rich double bond to afford the trans-vinylcyclopropane; an allylic hydroxyl group increases the reactivity and directs the cyclopropanation to the adjacent double bond.

Full text of DOI:10.1080/00397919608002620

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Synthetic Communications: An
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Organic Chemistry
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Site and Stereoselectivity
of the Cyclopropanation
of Unsymmetrically
Substituted 1,3-Dienes by the
Simmonssmith Reaction.
Mário César Guerreiro a & Ulf Schuchardt a
a Instituto de Química, Universidade Estadual de
Campinas , Cx. P. 6154, 13083-970, Campinas, SP,
Brazil
Published online: 21 Aug 2006.
To cite this article: Mário César Guerreiro & Ulf Schuchardt (1996) Site and
Stereoselectivity of the Cyclopropanation of Unsymmetrically Substituted 1,3-Dienes
by the Simmonssmith Reaction. , Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 26:9, 1793-1800, DOI:
10.1080/00397919608002620
To link to this article: http://dx.doi.org/10.1080/00397919608002620
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