Table 2.

Catalytic enantioselective crotylation of N-benzyl isatins 1a–1g via iridium catalyzed C-C bond forming transfer hydrogenation.

Entry	Isatins 1a–1g	Products	Yield (%)	ee (%), dr
1b	1a, N-benzyl isatin	3a	83	80, 13:1
2f	1b, 5-bromo-N-benzyl isatin	3b	72	86, 16:1
3d,e	1c, 5-methyl-N-benzyl isatin	3c	81	89, 18:1
4d,e	1d, 5-methoxy-N-benzyl isatin	3d	87	92, 29:1
5b	1e, 6-chloro-N-benzyl isatin	3e	70	91, 19:1
6f	1f, 6-bromo-N-benzyl isatin	3f	81	89, 15:1
7b,c	1g, 7-fluoro-N-benzyl isatin	3g	64	85, 19:1

^aAs described in Table 2 footnotes.

^b10 mol% loading of Cs₂CO₃ was used.

^c400 mol% loading of allyl acetate was used.

^dMe-THF was used as solvent.

^eThe reaction was run for 40 hours.

^f5 mol% loading of [Ir(cod)Cl]₂, 10 mol% loading of CTH-(R)-P-PHOS and 20 mol% loading of 4-CN-3-NO₂-BzOH were used.