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. Author manuscript; available in PMC: 2010 May 13.
Published in final edited form as: J Am Chem Soc. 2009 May 13;131(18):6318–6319. doi: 10.1021/ja8097349

Table 2.

Syntheses of Tetrahydropyridinesa

graphic file with name nihms111744t2.jpg
entry R1 R2 product yield
(%)b 		dr
(trans/cis)c
1 H (1b) 2-MeC6H4 3b 88 90:10
2 H (1c) 3-MeC6H4 3c 82 86:14
3 H (1d) 4-MeC6H4 3d 64 89:11
4 H (1e) 2,4-Me2C6H3 3e 82 81:19
5 H (1f) 2,5-Me2C6H3 3f 98 92:8
6 H (1g) 4-FC6H4 3g 76 88:12
7 H (1h) 2-ClC6H4 3h 46 97:3
8 H (1i) 3-ClC6H4 3i 86 83:17
9 H (1j) 4-ClC6H4 3j 84 90:10
10 H (1k) 3-BrC6H4 3k 58 85:15
11 H (1l) 4-BrC6H4 3l 75 88:12
12 H (1m) 2-naphthyl 3m 58 85:15
13 Me (1n) H 3n 66 41:59
14 H (1o) H 3o 37 N/A
a

All reactions were performed using 0.1 mmol of the aziridine and 4.8 equiv of the allenoate.

b

Isolated yields.

c

Diastereoisomeric ratio determined using HPLC (internal standard: 2-bromopyridine).