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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 3.

graphic file with name nihms62422f7.jpg
entry homoallylic alcohol imine 1,5-aminoalcohola yield (%) dr piperidineb (yield)
1 graphic file with name nihms62422t22.jpg
33 		ent-28 graphic file with name nihms62422t23.jpg
34c 		76 ≥50:1 graphic file with name nihms62422t24.jpg
35 (79%)
2a graphic file with name nihms62422t25.jpg
33 		28 graphic file with name nihms62422t26.jpg
36c 		30 4:1:1
2b 85 6:3:1
3 graphic file with name nihms62422t27.jpg
38 		28 graphic file with name nihms62422t28.jpg
36c 		88 35:4:1 graphic file with name nihms62422t29.jpg
37(78%)
4 graphic file with name nihms62422t30.jpg
38 		ent-28 graphic file with name nihms62422t31.jpg
39 		76 19:12:4:1
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) (−30 to 0 °C (entries 1, 2a, 3 and 4) or rt (entry 2b)).

b

Reaction conditions for cyclization: 1) H2 (1 atm), Pd(OH)2, AcOH/MeOH (1:10 v/v), rt, 2) 2-NsCl, Et3N, DMAP, CH2Cl2, 0 °C to rt, 3) PPh3, DIAD, THF, rt. Ar = 2-nitrophenyl.

c

Major diastereomer shown.

d

Cyclization of 36 to 37 was performed with the enantiomer of 36 (for data on ent-37, see Supporitng Information).