Table 2.

Morpholine Synthesis Scope^a

entry	substrate	nucleophile	product (dr)b	yieldc
1		TsNH2		80%
2	1c, R1 = CH3, R2 = Ts	TsNH2		73%
3	1d, R1 = i-Pr, R2 = Ts	TsNH2		82%
4	1e, R1 = CH2OTBS, R2 = Ts	TsNH2		72%
5	1f, R1 = CH2SBn, R2= Ts	TsNH2		42%
6	1g, R1 = Bn,R2 = Ns	TsNH2		83%
7	1h, R1 = Bn,R2 = Ms	TsNH2		73%
8		TsNH2		67%
9	1a, R1 = Bn; R2 = Ts	NsNH2		82%
10	1a	PMBSNH2		82%
11d	1a	MsNH2		43%
12	1a	SESNH2		98%
13d	1a	PhC(O)NH2		87%
14d	1a	NaN3		53%
15e	1c	PhC(O)NH2		73%
16f		TsNH2		52%

^aSame conditions as Table 1, entry 4 unless otherwise noted.

^bDiastereoselectivity obtained by analysis of the crude ¹H NMR spectra.

^cIsolated yields.

^dReaction was run using 4 equiv Cu(eh)₂.

^eReaction was run using 3 equiv of Cu(eh)₂.

^fReaction was run at 150 °C.