Table 1. 1,5-amino alcohols and piperidines via homoallylic alcohol– imine coupling.

entry	homoallylic alcohol	1,5-aminoalcohola	yield (%)	rr	dr	piperidineb(yield)
1			76	≥95:5	n/a
2			73	≥95:5	≥95:5
3			63	≥95:5	≥95:5
4			67	≥95:5	4:1

^aReaction 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).

^bReaction conditions for cyclization: PPh₃, imidazole, CCl₄, reflux.