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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 2.

graphic file with name nihms62422f6.jpg
entry homoallylic alcohol imine 1,5-aminoalcohola yield (%) dr piperidineb (yield)
1 graphic file with name nihms62422t14.jpg
14 		graphic file with name nihms62422t15.jpg
28 		graphic file with name nihms62422t16.jpg
29 		83 24:1 graphic file with name nihms62422t17.jpg
30 (77%)
2 graphic file with name nihms62422t18.jpg
27 		28 graphic file with name nihms62422t19.jpg
31 		75 20:1 graphic file with name nihms62422t20.jpg
32 (87%)
3 graphic file with name nihms62422t21.jpg
18 		28 31 61 25:4:1
a

Reaction conditions for cross coupling: imine (1 eq), Ti(Oi-Pr)4 (1.5 eq), c-C5H9MgCl (3.0 eq), Et2O (−60 to −30 °C), then add alkoxide (1.5 eq) (−40 to 0 °C or rt).

b

Reaction conditions for cyclization: For 30 - 2-NsCl, Et3N, DMAP, CH2Cl2, rt. For 32-MsCl, Et3N, CH2Cl2, rt. R = CH(Ph)CH2OMe.