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. Author manuscript; available in PMC: 2013 Sep 21.
Published in final edited form as: J Org Chem. 2012 Sep 6;77(18):8257–8267. doi: 10.1021/jo3015825

Table 1.

Optimization of Dihydroquinoline Synthesisa

graphic file with name nihms404426t1.jpg
entry 2a
(equiv)		 PPh3
(mol%)		 solvent concentrationb
(M)		 time
(h)		 yield
(%)
1 2.0 20 THF 0.1 17 28
2 c 2.0 20 THF 0.1 17 28
3 2.0 20 THF 0.1 24 32
4 2.0 100 THF 0.1 24 0
5 2.0 20 THF 0.05 17 25
6 2.0 20 THF 0.2 17 67
7 2.0 20 THF 0.4 17 68
8 2.0 20 MeCN 0.2 17 71
9 2.0 20 MeCN 0.4 N/Ad N/Ad
10 2.0 10 MeCN 0.2 17 75
11 2.0 5 MeCN 0.2 17 49
12 2.5 5 MeCN 0.2 17 47
13 2.0 10 MeCN 0.2 4 76
14 1.5 10 MeCN 0.2 4 76
15 1.2 10 MeCN 0.2 4 14
a

Butynone 2a was added in one portion to a solution of 1a and PPh3 in the indicated solvent.

b

Concentration of the aldehyde 1a.

c

Addition of butynone 2a over 2 h via syringe pump.

d

Not available.