Abstract
AbstractDibromocyclopropanes can be ring‐opened by utilizing zinc dibromide in catalytic amounts and iron powder in substoichiometric amounts. The presence of the carbonyl group of aldehydes, ketones, glyoxylic esters, or imines is necessary for the ring‐opening reaction. The ring opening leads to a bromo‐functionalized 1,3‐diene, which then reacts in situ with the carbonyl group in a hetero‐Diels–Alder reaction. The products are formed with high control of the regiochemistry and in good yields for electron‐deficient aldehydes and imines, such as carbamates. The application of (E)‐ethyl 2‐(methoxycarbonylimino)acetate led to a cyclic α‐amino acid derivative. The use of unsymmetrical dibromo‐ and dihalocyclopropanes is also reported.
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