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Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84
Graphical Abstract
Scheme 1: Examples of drugs containing a γ-lactam and derivative.
Scheme 2: Desymmetrization strategies employing Heck-Matsuda reactions.
Scheme 3: Heck–Matsuda reaction (1) and Jones oxidation (2) of the N-Boc-protected 2,5-dihydro-1H-pyrrole 1a....
Figure 1: N,N-Ligands evaluated in this work.
Scheme 4: Heck–Matsuda reaction of N-tosyl-2,5-dihydro-1H-pyrrole (1b). Reaction conditions: 1) pyrroline 1b ...
Scheme 5: Heck–Matsuda reaction of the protected 2,5-dihydro-1H-pyrrole with Ns and 2-Ns groups (pyrrolines 1c...
Scheme 6: Synthesis of (R)-baclofen hydrochloride (6) from 4dd and (R)-rolipram (5b) from 4de. Reaction condi...
Scheme 7: A rationale for the catalytic cycle for the Heck–Matsuda reaction of the protected 2,5-dihydro-1H-p...
Figure 2: Rationalization of the enantioselectivity obtained in the Heck–Matsuda reaction of protected 2,5-di...