Table 1.

Ni/NMDPP-Catalyzed Reductive Coupling of 1-Phenyl-1-propyne (1a) and MOM-Protected α-Oxyaldehyde 2a

entrya	phosphine	time(h)	temp (°C)	d.rb	yield (%)(d.r.)c
1	(+)-NMDPP	6	0	84:16	61 90:10)
1	(-)-NMDPP	6	0	77:23	32 (80:20)
3	(+)-NMDPP	6	-10	89:11	62 (90:10)
4	(+)-NMDPP	6	-20	90:10	37 (90:10)
5d	(+)-NMDPP	6	-10	89:11	77 (90:10)
6d	(+)-NMDPP	20	-10	88:12	87 (90:10)

^aSee Supporting Information for experimental procedures. 100 mol% of alkyne and 100 mol% of aldehyde were used, unless otherwise noted. All reactions proceeded with >95:5 regioselectivity.

^bRatio of anti:syn determined by ¹H NMR analysis of crude reaction mixtures.

^cYield and d.r. of the isolated reaction product.

^dConducted using 150 mol% of aldehyde.