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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 2.

Catalytic Asymmetric Conjugate Allylation of Methylidene Ketones in the Presence of (R,R,S)-L6.a

graphic file with name nihms278009u3.jpg
entry product regiob % yieldc erd
1 graphic file with name nihms278009t1.jpg >100:1 59 93:7
2 graphic file with name nihms278009t2.jpg >100:1 79 94:6
3 graphic file with name nihms278009t3.jpg >100:1 57 95:5
4 graphic file with name nihms278009t4.jpg >100:1 91 91:9
5 graphic file with name nihms278009t5.jpg >100:1 53 91:9
6e graphic file with name nihms278009t6.jpg >100:1 81 96:4
7 graphic file with name nihms278009t7.jpg >100:1 80 95:5
8 graphic file with name nihms278009t8.jpg >100:1 37 96:4
9 graphic file with name nihms278009t9.jpg >100:1 76 95:5
a

Unless otherwise noted, the reaction was carried out at room temperature for 14 h and quenched with saturated NH4Cl(aq) or acetic acid.

b

Regioselectivity determined by uncalibrated GLC analysis in comparison to authentic materials.

c

Isolated yield after purification. Value is an average of two or more experiments.

d

Enantiomer ratio determined by GLC, SFC or HPLC analysis.

e

Experiment for 48 h and quenched with glacial acetic acid at 45 °C for 3 h.