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. Author manuscript; available in PMC: 2012 Oct 7.
Published in final edited form as: Org Lett. 2011 Sep 12;13(19):5322–5325. doi: 10.1021/ol2021862

Table 2.

Synthesis of 5-phenylmorphans 8b-j using substituted allyl halides 5b-i

entry allyl halide yield (%) product
1 graphic file with name nihms-324932-t0007.jpg 56 graphic file with name nihms-324932-t0008.jpg
2 graphic file with name nihms-324932-t0009.jpg 49 graphic file with name nihms-324932-t0010.jpg
3 graphic file with name nihms-324932-t0011.jpg 41 graphic file with name nihms-324932-t0012.jpg
4 graphic file with name nihms-324932-t0013.jpg 65 graphic file with name nihms-324932-t0014.jpg
5 graphic file with name nihms-324932-t0015.jpg 64 graphic file with name nihms-324932-t0016.jpg
6 graphic file with name nihms-324932-t0017.jpg 52 graphic file with name nihms-324932-t0018.jpg
7 graphic file with name nihms-324932-t0019.jpg 39a,b graphic file with name nihms-324932-t0020.jpg
8 graphic file with name nihms-324932-t0021.jpg 60
(0)c
graphic file with name nihms-324932-t0022.jpg
9 graphic file with name nihms-324932-t0023.jpg 36d
(31)e
graphic file with name nihms-324932-t0024.jpg
a

Diastereomeric mixture.;

b

20% of 8f was also obtained.;

c

When the original reaction conditions (HCO2H/H3PO4, 1:1) were used, the desired product was not obtained;

d

Not isolated - NMR and MS indicated product;

e

Yield of the cyclized enamine 7i;

f

Yield of 8j after reduction of 7j.