Synthesis of (2S, 3R, 4S)-3,4-methanoproline and analogues by cyclopropylidene insertion

Efficient Synthesis of Cyclopropane‐Fused Heterocycles with Bromoethylsulfonium Salt

“…[9] Numerous methods have been developed for the construction of azabicyclo[3.1.0]hexanes. [10] These include the Kulinkovich/de Meijere reaction [11,12] , cyclisation of tethered amines with metals (Pd [13] , Ru [14] , Rh [15] , Ag [16] ), cyclisation of tethered cyclopropanes [17] , and the Simmons-Smith [18] /CoreyChaykovsky [19] /sulfur ylide-Au [20] cyclopropanations. These methods are usually only effective in the synthesis of one specific type of scaffold.…”

Preparative resolution of bromocyclopropylcarboxylic acids

“…Chiral halocyclopropanes are useful building blocks and convenient precursors for chiral cyclopropyl anions 2 (Scheme 1, path a), 1 cyclopropylidenes 3 (path b), 2 and cyclopropenes 4 (path c). 3 They can also be engaged in transition-metal catalyzed crosscoupling reactions (path d).…”

“…4 These synthons are also important for the assembly of cyclopropane-containing targets. 2,5,6 Their ability to participate in highly stereoselective ring-opening transformations 7 may be advantageously employed in the installation of stereodefined three carbon atom fragments.…”

Chiral methyl trans-2,2-dichloro-3-methylcyclopropanecarboxylate upon exposure to thiophenolate nucleophile

“…[1][2][3][4][5][6][7][8][9][10][11] These compounds are excellent building blocks due to their availability in high enantiomeric purity, simple techniques of preparation, and a substantial synthetic potential of the cyclopropane ring. [12][13][14][15] For example, they were utilized in the asymmetric synthesis of pyrethroids 1,2 and other natural products, 3,4 stereoregular oligocyclopropanes, 5 chiral biaryls, 6 and liquid crystals. 7 In a recent article we efficiently resolved racemic trans-2,2-dichloro-3-methylcyclopropanecarboxylic acid into enantiomers 1.…”