Table 2. Diastereoselective McMurry Coupling Using Zn as Reductant.

entry	R1	R2	ee of ketone (% ee)a	yield (%)b	product	E/Zc	ee (% ee)d
1	H	Br (2)	97	85	11	50/50	99
2	H	Br (2)	94	82	11	45/55	97
3	H	Br (2)	89	75	11	50/50	93
4	Br	H (3)	94	89	12	40/60	98
5	H	H (1)	81	86	13	25/75	91
							Z: 85
6	H	OTBS (4)	97	92	14	50/50	99e
							Z: 99e
7	OTBS	H (5)	96	90	15	44/56	97e

^aDetermined by chiral-HPLC or SFC.

^bIsolated yields.

^cDetermined by ¹H NMR.

^dEnantiomeric excess of E-isomer if not stated otherwise, determined by chiral-HPLC or SFC.

^eDetermined after TBS deprotection.