Table 1 Pd-catalyzed carbene coupling between N-tosylhydrazone with benzyl bromide

Reaction conditions: the reaction was carried out at 0.1 mmol scale with palladium (5.0 mol%), L* (10.0 mol%), LiOtBu (3.0 equiv.), and the solvent (1.0 mL) in a sealed vial at 60 °C for 20 h, and the molar ratio of 1a:2a was 1:1.2.
^aIsolated yield.
^bDetermined by chiral HPLC.
^cThe reaction was performed at 50 °C for 36 h.
^dPd₂(dba)₃ (2.5 mol%), L7 (5.0 mol%), reaction time: 48 h.
^eBenzyl chloride (0.12 mmol) was used instead of 2a (2.5 mol%), L7 (5.0 mol%), reaction time: 48 h.

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