Table 2.

Iridium-catalyzed N-allylation of 2-substituted, 3-substituted, and 2,3-disubstituted indoles 4b–p with tert-butyl cinnamyl carbonate 3a.^[a]

Entry	4	R1	R2	R3	5	5/6[b]	Yield [%][c]	ee [%][d]
1	4b	CO2Et	H	OMe	5l	97:3	88	99
2	4c	CO2Et	H	F	5m	94:6	84	99
3	4d	CO2Et	H	Cl	5n	95:5	91	99
4	4e	CO2Et	H	NO2	5o	94:6	90	99
5	4f	CHO	H	H	5p	98:2	89	99
6	4g	H	CO2Me	H	5q	96:4	84	97
7	4h	H	CHO	H	5r	94:6	87	96
8	4i	H	C(O)Me	H	5 s	98:2	88	96
9	4j	H	CN	H	5t	96:4	93	96
10	4k	H	Ph	H	5u	99:1	21	97
11	4 l	CHO	Me	H	5v	98:2	82	99
12	4m	Ph	CHO	H	5w	96:4	93	97
13	4n	Ph	Ph	H	5x	98:2	95	99
14	4o	Ph	Me	H	5y	98:2	89	99
15	4p	-(CH)4-		H	5z	98:2	88	98

^[a]See the Supporting Information for experimental details.

^[b]Determined by ¹H NMR analysis of the crude reaction mixture.

^[c]Yield of isolated 5.

^[d]Determined by chiral HPLC methods.

^[e]Methyl cinnamyl carbonate was used as the electrophile.