Table 1.

Enaminone Allylic Alkylation Screen.^[a]

					Enantiomeric Excess (% ee)[b]
entry	Substrate	R	Product	ligand	THF	MTBE	Toluene	2:1 Hex–Tol
1	9a	H	13a	3	87	88	87	87
2				8	85	86	88	85
3	10a	Oi-Bu	14a	3	85	85	86	87
4				8	86	86	86	88
5	12a	NMe(Bn)	15a	3	61	60	55	52
6				8	79	78	84	83
7	12b	NPh(Bn)	15b	3	81	87	85	83
8				8	76	74	82	83
9	12c	NAc(Bn)	15c	3	89	90	88	88
10				8	83	85	88	86
11	12d	NBz(Bn)	15d	3	86	87	88	87
12				8	80	83	82	83
13	12e	NBoc(Bn)	15e	3	87	86	87	82
14				8	84	84	81	83
15	12f	NTs(Bn)	15f	3	84	83	83	82
16				8	82	83	83	83

^[a]Conditions: enone 9a, vinylogous ester 10a, or enaminone 12a–f (1.0 equiv), Pd₂(dba)₃ (5 mol %), and (S)-t-BuPHOX (3) or (S)-(CF₃)₃-t-BuPHOX (8) (12.5 mol %) in solvent (0.033 M) at 40 °C.

^[b]Determined by GC, HPLC, or SFC analysis with chiral stationary phase.

Red = with (S)-3 as ligand and blue = with (S)-8 as ligand.