Table 1. Reaction Development.

entrya,b	R	Pd catalyst (10 mol%)	L.A. co-catalyst (8 - 10 mol%)	Yield of 4 (%)c,d	Yield of 5 (%)c,d	4:5
1e	Ns	1	none	19%	28%	1:1.6
2f	Ns	1	DIPEA	0%	38%	1:>20
3e	Ns	1	B(C6F6)3	50%	7%	4.9:1
4g	Ns	1	AgOTf	76%	9%	7:1
5h	Ns	1	Cr(salen)Cl	8%	8%	1:1
6g	Ts	1	AgOTf	56%	trace	>20:1
7g	Ns	1	TfOH	64%	28%	2.3:1
8i	Ns	none	TfOH	0%	0%	-
9g,i	Ns	none	AgOTf	0%	0%	-
10e	Ns	2	AgOTf	0%	46%	1:>20	Pd(OAc)2 cat. 2
11 j	Ns	2	AgOTf	0%	59%	1:>20
12j	Ns	2	B(C6F6)3	0%	62%	1:>20
13j	Ns	2	none	0%	32%	1:>20
14i,j	Ns	none	B(C6F6)3	0%	0%	-

^aAll reactions were run using THF (1.0M) as solvent, MeBQ (methyl-p-benzoquinone, 1.5 equiv.) as terminal oxidant and 8 mol% L.A. co-catalyst for 6 hours unless otherwise noted.

^bReactions with cat. 1 were run with an additional 5 mol% BisSO ligand [1,2-bis(phenylsulfinyl)ethane].

^cAverage of 2 runs.

^dObserved diastereoselectivities in crude reaction mixtures: >20:1 dr for 4 for all entries; dr for 5: entry 1, 1.3:1 dr anti:syn; entry 2, 4.4:1 dr; entry 4, 1:1 dr; entries 3, 5, 10, 11, 12, 13 >20:1 dr; dr determined by ¹H NMR analysis of the crude reaction mixture.

^eReactions run to complete conversion: entry 1, 24h; entry 3, 2h; entry 10, 72h.

^fReaction stopped at 18h (37% rsm); no improved conversion was observed at 48h or 72h.

^gDCM (dichloromethane, 1.0M); For entry 4, 1 equiv. of DMA was added.

^hReaction stopped before complete conversion at 2h. Increased reaction times resulted in product decomposition.

ⁱ>99% rsm, 0% E-internal olefin.

^jReaction run using THF (1.66M) as solvent, BQ (p-benzoquinone, 1.05 equiv.) as terminal oxidant and 10 mol% L.A. co-catalyst for 72 hours.