Stereoselective synthesis of 3,4-diaryl β-lactams

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

“…All work was carried in a well ventilated fumehood, with an automatic shut down of the system in case of an increase of the temperature and pressure over the maximum value set. The spectroscopic data of trans-6a, 62 trans-6d, 20 trans-6g, 63 trans-6i, 55 cis-6j, 64 trans-6m, 55 and trans-6n, 65 are in accordance with reported values.…”

Chemical Synthesis of β-Lactams: Asymmetric Catalysis and Other Recent Advances

“…Troisi and co-workers published a palladium-catalyzed cyclocarbonylation of benzyl halides and imines 142 to synthesize 3,4-diaryl β-lactams that is an extension of work by Torii and co-workers in 1993 (using allyl phosphates). 143 Benzyl bromides and chlorides were reacted with alkyl-and aryl-substituted imines with catalytic palladium(II) acetate, triphenylphosphine, and triethylamine in a CO atmosphere (400 psi) at 100 °C for 60−90 h to generally give either cis or trans β-lactams in good diastereoselectivity, contingent upon the nature of the substituents (Scheme 43).…”

Palladium-Catalyzed Carbonylative Transformation of C(sp3)–X Bonds

“…Based on the work of allyl halides carbonylation and [2 + 2] cycloaddition with imines, Troisi and co-workers reported in 2009 a palladium-catalyzed stereoselective synthesis of 3,4-diaryl β-lactams from benzyl halides and imines (Scheme ) . Benzyl bromides were found to react faster than benzyl chlorides but delivered similar yields of β-lactams.…”