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. Author manuscript; available in PMC: 2014 Feb 20.
Published in final edited form as: J Am Chem Soc. 2013 Feb 7;135(7):2501–2504. doi: 10.1021/ja400506j

Table 1.

Tandem diene diboration/double allylation of dicarbonyls.a

graphic file with name nihms444012t1.jpg
entry R1 R2 dicarbonyl product d.r.
e.r.
yield
1 prenyl Me graphic file with name nihms444012t2.jpg graphic file with name nihms444012t3.jpg 5:1 dr
6:4 er
76 %
2 Me prenyl graphic file with name nihms444012t4.jpg graphic file with name nihms444012t5.jpg 2.8:1 dr
96:4 er
83%
3 prenyl Me graphic file with name nihms444012t6.jpg graphic file with name nihms444012t7.jpg 1.2:1 dr
97:3 er
72%
4b Me CH2OSiR3 graphic file with name nihms444012t8.jpg graphic file with name nihms444012t9.jpg 10:1 dr
97:3 er
71%
5 pentyl H graphic file with name nihms444012t10.jpg graphic file with name nihms444012t11.jpg >20:1 dr
91:9 er
39%
6 -(CH2)5- graphic file with name nihms444012t12.jpg graphic file with name nihms444012t13.jpg 9:1 dr
88:12 er
72%
7 Me prenyl graphic file with name nihms444012t14.jpg graphic file with name nihms444012t15.jpg 11:1 dr
97:3 er
77%
8 Me prenyl graphic file with name nihms444012t16.jpg graphic file with name nihms444012t17.jpg >20:1 dr
97:3 er
60%
9 Me prenyl graphic file with name nihms444012t18.jpg graphic file with name nihms444012t19.jpg >20:1 dr
97:3 er
54%
a

Entries 1, 4, and 6 employed 2 equivalents of dicarbonyl; entries 2, 3, 7, and 8 employed 1 equiv. dicarbonyl; entry 5 employed 3 equiv dicarbonyl; entry 9 employed 2 equivalents of diene/B2(pin)2. Diastereoselectivity determined by 1H NMR analysis; yield refers to isolated yield of the regioisomer mixture.

b

(S,S) ligand employed for this experiment.