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. Author manuscript; available in PMC: 2016 Sep 2.
Published in final edited form as: Tetrahedron. 2015 Sep 2;71(35):5886–5896. doi: 10.1016/j.tet.2015.05.021

Table 3.

Synthesis of indanones via Nazarov cyclization

# Starting material Conditions Product Yield; dr
(trans:cis)
1 graphic file with name nihms696081t2.jpg 5 mol %
Cu(OTf)2,
DCE, 60
°C
graphic file with name nihms696081t3.jpg 81%;
>20:1
2 graphic file with name nihms696081t4.jpg 5 mol %
Cu(ClO4)2,
DCE, 45
°C
graphic file with name nihms696081t5.jpg 75%;
>20:1
3 graphic file with name nihms696081t6.jpg 5 mol %
Cu(ClO4)2,
DCE, rt
graphic file with name nihms696081t7.jpg --a;
3:1
4 graphic file with name nihms696081t8.jpg cat.
Sc(OTf)3/
Li(ClO4),
DCE, 45
°C
graphic file with name nihms696081t9.jpg 81%;
3:1
5 graphic file with name nihms696081t10.jpg cat.
Sc(OTf)3/
Li(ClO4),
DCE, 45
°C
graphic file with name nihms696081t11.jpg -b
6 16d (TMS)NTf2 18d -b
7 16d 1.1 eq.
AlCl3,
DCE, 0 °C
18d 71%;
3.6:1
8 16d 1.1 eq.
Sc(OTf)3,
DCE, rt
18d 46%;
3.6:1
9 graphic file with name nihms696081t12.jpg 1.1 eq.
AlCl3,
DCE, 0 °C
18d ~70–75%;
3.6:1
a

See Experimental section

b

Decomposition