Fig. 5: Synthetic applications. | Nature Communications

Fig. 5: Synthetic applications.

From: Rhodium-catalyzed construction of boron-based point and axial chirality via asymmetric annulation of alkynylborons

Fig. 5: Synthetic applications.The alternative text for this image may have been generated using AI.

a Scope of [3 + 2] annulation of nitrones bearing a bioactive or drug moiety. aReaction conditions: nitrone (0.12 mmol), alkyne (0.10 mmol), (R)-Rh3 (4 mol%), AgBF4 (16 mol%) and CCA (50 mol%) in toluene (2 mL), 0 °C, 48 h; bnitrone (0.12 mmol), alkyne (0.10 mmol), (R)-Rh3 (4 mol%), AgOTf (16 mol%) and MesCOOH (2 equiv) in toluene (2 mL), 25 °C, 48 h. b Scale-up synthesis and synthetic transformations of a selected product. reaction conditions c: 72 (0.10 mmol), p-tolylboronic acid (0.20 mmol), Pd(PPh3)4 (4 mol%) and Na2CO3 (0.2 mmol) in toluene:EtOH:H2O (2 mL, 10:1:1), 60 °C, 12 h; Reaction conditions d: 72 (0.10 mmol), Pd(OAc)2 (5 mol%), dppf (10 mol%), HCOOH (0.25 mmol) and Et3N (0.3 mmol) in DMF (2 mL), 50 °C, 3 h. c Applications of chiral phosphine ligand.

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