Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

Aminocyclopropanes as precursors of endoperoxides with antimalarial activity

“…8 However, previous work, carried out with simpler substrates (R 2 = H; R 3 π H), has established that R 3 groups fitted with a coordinating function, such as a benzyloxy or a methoxy group, located at a suitable distance from the C C double bond, can overcome this impediment. 9 With these requirements, the new N-alkenyl amides 3c, 3d and 3f were synthesised using cross-metathesis reactions from the corresponding known simpler molecules 3b and 3e, 10 for which the carbon-carbon double bond is monosubstituted (R 3 = H) (Scheme 2). The two diastereoisomeric diamides (R*,R*)-3g (chiral) and (R*,S*)-3g (not chiral) were produced by homo-cross metathesis of 3b (Scheme 3).…”

Cyclization of Zincated α‐N‐Homoallylamino Nitriles: A New Entry to Enantiopure 2,3‐Methanopyrrolidines

“…[13][14][15][16] If successful, our approach would thus offer a new entry to enantiopure 2,3-methanopyrrolidines (Scheme 1), which are interesting compounds [12,17] that are still challenging to prepare in spite of recent elegant approaches based on the intramolecular Kulinkovich-de Meijere reaction. [18]…”

Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible‐Light Photocatalysis

“…Bicyclic cyclopropylamines 5a–f were readily prepared from their corresponding amides by the Kulinkovich–de Meijere reaction. [11a,21] In contrast to monocyclic tertiary cyclopropylanilines, bicyclic tertiary cyclopropylanilines 5a–f successfully underwent the cycloaddition with styrene ( 2a ) to provide fused saturated heterocycles 6a–f in synthetically useful yields and diastereoselectivities (Table 3). The drastic difference in reactivity between these two classes of cyclopropylamines was likely as a result of the higher ring strain in the bicyclic compounds.…”