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. Author manuscript; available in PMC: 2012 Mar 4.
Published in final edited form as: Org Lett. 2011 Feb 2;13(5):995–997. doi: 10.1021/ol102982b

Table 1.

Catalytic Conjugate Allylation of Methylidene Ketone 3 with Chiral Taddol-Derived Ligandsa

graphic file with name nihms278009u2.jpg
entry L R metal 4:5 % yield er 4
1 L1 Ph Ni(cod)2 14:1 21 77:23
2 L1 Ph Pd2(dba)3 17:1 22 48:52
3 L2 NMe2 Ni(cod)2 2.4:1 32 51:49
4 L2 NMe2 Pd2(dba)3 20:1 15 66:34
5 L3 N(CH2)5 Ni(cod)2 1.5:1 44 50:50
6 L3 N(CH2)5 Pd2(dba)3 35:1 10 75:25
7 L4 N(CH2)6 Pd2(dba)3 63:1 50 76:24
8 L5 NBn2 Pd2(dba)3 >100:1 14 75:25
a

Reactions were quenched by addition of H2O. Regioisomer ratio and enantiomer ratio were determined by GLC analysis.