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. Author manuscript; available in PMC: 2012 Dec 21.
Published in final edited form as: J Am Chem Soc. 2011 Nov 30;133(50):20611–20622. doi: 10.1021/ja209244m

Table 1.

Initial Optimization of Pd-Precatalyst and Chiral Ligand

graphic file with name nihms338081u1.jpg
entry precatalyst ligand % yielda d.r.b eec
1 none none NR n.a. n.a.
2 [Pd(allyl)Cl]2 (R,R)-L1 68 (93) 4.2:1 66
3 [Pd(allyl)Cl]2 (R,R)-L2 60 (82) 1.4:1 65
4 [Pd(allyl)Cl]2 (R,R)-L3 65 (88) 1.6:1 63
5 [Pd(allyl)Cl]2 (R,R)-L4 74 (88) 1:2.7 15
6d [Pd(allyl)Cl]2 (R,R)-L1 75 (88) 4.2:1 66
7d Pd(OTFA)2 (R,R)-L1 NR n.a. n.a.
8d Pd(OAc)2 (R,R)-L1 61 (95) 4.6:1 67
9d Pd2(dba)3-CHCl3 (R,R)-L1 80 (94) 6.2:1 78
10e Pd2(dba)3-CHCl3 (R,R)-L1 92 6.4:1 80
a

Determined by 1H NMR with respect to mesitylene as the internal standard, number in parantheses refers to yield based on unreacted 10.

b

Determined by 1H NMR of the unpurified reaction mixture.

c

Determined by chiral HPLC analysis.

d

Using 1.2 equiv 4.

e

Using 1.2 equiv of freshly prepared 4.