cyclopropyl1





1) Formation of the lithium enolate 2) aldol condensation 3) reduction 4) halogenation via Tosyl Ester intermediate 5) SN2 via sodium methoxide 6) cyclopropane ring formation via Zinc Coupled catalyst

By: Naomi, Tiffany, Sandra

This is a very nice use of reactions that we have studied, and some that we haven't. The aldol, condensation that is covered in Chapter 2 is one of a whole class of reactions that are used extensively in synthesis. The use of lithium diisopropyl amide prevents the acetone from adding to the ethaldehyde. Alternatively you can treat the aldehyde with a secondary amine to make the enamine, which is also highly nucleophilic. Please ad references to literature, including Wade. Bruce Bondurant

Sources:

Winter, Arthur. // Organic Chemistry I for Dummies //. Indianapolis: Wiley. Hathaway, Bruce A. // Organic Chemistry: The Easy Way //. Hauppauge: Barron's Educational Series, 2005. Bloch, Daniel R. // Organic Chemistry Demystified //. McGraw-Hill Companies, 2005. Wade pgs 353-355, 232-242, 272, 316-317, 376-377