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. Author manuscript; available in PMC: 2012 Sep 16.
Published in final edited form as: J Org Chem. 2011 Aug 23;76(18):7614–7617. doi: 10.1021/jo2013753

Table 1.

Enantioselective Allylation of Cyclic Enones.

Enonea Yieldb Product ee
1 graphic file with name nihms320427t1.jpg
1a
84% graphic file with name nihms320427t2.jpg
3a
98% ee
2 graphic file with name nihms320427t3.jpg
1bc,d
46% graphic file with name nihms320427t4.jpg
3b
97% ee
3 graphic file with name nihms320427t5.jpg
1c
92% graphic file with name nihms320427t6.jpg
3c
93% ee
4 graphic file with name nihms320427t7.jpg
1d
95% graphic file with name nihms320427t8.jpg
3d
92% ee
5 graphic file with name nihms320427t9.jpg
1e
89% graphic file with name nihms320427t10.jpg
3e
85% ee
a

Additions were carried out using 5 mol % (S)-3,3′-dibromobinol.

b

Yields are for pure isolated substances.

c

Addition was effected using 5 mol % (R)-3,3′-dibromobinol.

d

Both the starting material and the product were volatile.