A highly diastereoselective protocol for the synthesis of chiral multisubstituted cyclopropanes from 1-bromocyclopropylcarboxamides (1) will be described.Diastereoselectivity in addition of nucleophiles to in situ generated cyclopropenes (2) can be achieved via steric and directing control, leading to two different types of cyclopropanes. Existing stereogenic center at C-2 of the bromocyclopropane sets two other stereocenters on the cyclopropane via the dual control strategy, utilization of several types of control on one substrate. The possibilities of steric/thermodynamic and directing/thermodynamic dual control strategies will be discussed. Scope and limitation of the methodology will be discussed in detail and the mechanistic implications will be provided.

Dual control of selectivity in the synthesis of homochiral densely substituted cyclopropanes via the addition of nucleophiles to in situ generated cyclopropenes

245th National Meeting (2013)

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