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. Author manuscript; available in PMC: 2009 Aug 26.
Published in final edited form as: J Am Chem Soc. 2007 May 26;129(24):7514–7516. doi: 10.1021/ja071974v

Table 1.

graphic file with name nihms62422f5.jpg
entry homoallylic alcohol imine 1,5-aminoalcohola yield (%) rr dr piperidineb (yield)
1 graphic file with name nihms62422t1.jpg
14 		graphic file with name nihms62422t2.jpg
15 		graphic file with name nihms62422t3.jpg
16 		76 ≥95.5 n/a graphic file with name nihms62422t4.jpg
17 (85%)
2 graphic file with name nihms62422t5.jpg
18 		15 graphic file with name nihms62422t6.jpg
19 		73 ≥95.5 ≥95.5 graphic file with name nihms62422t7.jpg
20 (81%)
3 graphic file with name nihms62422t8.jpg
21 		15 graphic file with name nihms62422t9.jpg
22 		63 ≥95.5 ≥95.5 graphic file with name nihms62422t10.jpg
23 (77%)
4 graphic file with name nihms62422t11.jpg
24 		15 graphic file with name nihms62422t12.jpg
25 		67 ≥95.5 4:1 graphic file with name nihms62422t13.jpg
26 (76%)
a

Reaction conditions for cross coupling: imine (1 eq), Ti(Oi-Pr)4 (1.5 eq), c-C5H9MgCl (3.0 eq), Et2O (−78 to −40 °C), then add alkoxide (1.5 eq) (−40 to −20 °C, 0 °C, or rt -see Supporting Information for details).

b

Reaction conditions for cyclization: PPh3, imidazole, CCl4, reflux.