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. Author manuscript; available in PMC: 2017 Nov 9.
Published in final edited form as: J Am Chem Soc. 2016 Oct 28;138(44):14570–14573. doi: 10.1021/jacs.6b09939

Table 1.

Scope of Multicomponent Carboamination of Tethered Enynes with PhNNPha

graphic file with name nihms868680u1.jpg

Substrate % Isolated Yieldb (2:3) 1H NMR % Yield (2:3)
1a graphic file with name nihms868680t1.jpg 50
(>99:1)
92
(85:15)
1b graphic file with name nihms868680t2.jpg 86
(44:56)
92
(53:47)
1c graphic file with name nihms868680t3.jpg 37
(>99:1)
d
1d graphic file with name nihms868680t4.jpg 13
(1: >99)e
29
(1: >99)
1e graphic file with name nihms868680t5.jpg 60
(>99:1)
91
(>99:1)
1f graphic file with name nihms868680t6.jpg 69
(>99:1)
86
(>99:1)
1g graphic file with name nihms868680t7.jpg 50
(>99:1)
d
1h graphic file with name nihms868680t8.jpg 54
(49:51)
d
1i graphic file with name nihms868680t9.jpg 57
(5:95)f
d
1j graphic file with name nihms868680t10.jpg 36
(1:>99)g
d
1k graphic file with name nihms868680t11.jpg 37
(1:>99)h
d
11 graphic file with name nihms868680t12.jpg 0 n.d.
1m graphic file with name nihms868680t13.jpg 0 n.d.
a

Loading of [py2TiCl2NPh]2 and reaction yields with respect to PhNNPh.

b

Isolated as the ketone product after hydrolysis. See SI for details.

c

Determined by 1H NMR analysis of the crude reaction mixture.

d

Could not be determined due to peak overlap in the 1H NMR spectrum.

e

Isolated as the retro-ene product 3d′ (Figure 3).

f

As a mixture of 2i, 3i and 4i (Figure 5).

g

As 4j.

h

As a mixture of 3k and 4k.