Table 11.

Coupling of Nitrogen-Containing Alkenes with Aldehydes ^a

entry	R1 (alkene)	R2 (aldehyde)	ligand	major product	yield (%) b	ratio (4:4′) b	ratio (E:Z) c
1		Ph	Cy2PhP	4a	67	74:26	-
			(EtO)Ph2P	4a′	43	12:88	60:40
2		o-anisyl	Cy2PhP	4b	54	71:29	-
			Ph3P	4b′	76	<5:95	83:17
3		Ph	Cy2PhP	4c	60	83:17	-
			(EtO)Ph2P	4c′	28	10:90	n.d.

^aStandard procedure: To a solution of Ni(cod)₂ (0.1 mmol) and ligand (0.2 mmol) in toluene (2.5 mL) at 23 °C under Ar were added the alkene (1.5 mmol), triethylamine (3.0 mmol), the aldehyde (0.5 mmol), and Et₃SiOTf (0.875 mmol). The mixture was stirred 48 h at room temperature and purified by chromatography (SiO₂).

^bDetermined by ¹H NMR of the crude reaction mixture using DMF as a standard.

^cThe ratio was determined by ¹H NMR of the mixture of E and Z homoallylic alcohols after the silyl group of the coupling product was removed by TBAF.