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. Author manuscript; available in PMC: 2010 Mar 1.
Published in final edited form as: Organic Synth. 2009 Mar 1;2009(86):212–224. doi: 10.1002/0471264229.os086.21

Table 2.

Synthesis of Tetrahydropyridines 9 From Ethyl 2-Arylmethyl-2,3-butadienaoates and N-Tosylaldiminesa

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entry R R ′ product yield (%)b drc
1d Ph (2) Ph (8a) 9a 92 98:2
2 Ph (2) 4-NCC6H4 (8b) 9b 99 98:2
3 Ph (2) 3-MeOC6H4 (8c) 9c 99 98:2
4 Ph (2) 2-FC6H4 (8d) 9d 99 97:3
5 Ph (2) 2-MeC6H4 (8e) 9e 82 88:12
6 4-MeOC6H4 (2a) Ph (8a) 9f 99 97:3
7 4-O2NC6H4 (2h) Ph (8a) 9g 90 95:5
8 2-F3CC6H4 (2g) 4-NCC6H4 (8b) 9h 80 90:10
9 3-ClC6H4 (2c) 4-NCC6H4 (8b) 9i 99 98:2
10 4-MeC6H4 (2b) 3-MeOC6H4 (8c) 9j 99 98:2
11 2-ClC6H4 (2d) 3-MeOC6H4 (8c) 9k 96 83:17
a

1.0 mmol scale.

b

Isolated yields.

c

Diastereoisomeric ratio, determined using 1H NMR spectroscopy.

d

30 mmol scale.