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. Author manuscript; available in PMC: 2015 Mar 6.
Published in final edited form as: Chemistry. 2013 Sep 3;19(39):12953–12958. doi: 10.1002/chem.201301731

Table 5.

[CoII(Por)]-catalysed trans-selective β-lactam synthesis using different N-tosylhydrazone sodium salts and imines.[a]

graphic file with name nihms667899t5.jpg
Entry Catalyst R R′ R″ Yield (%)[b]
(trans:cis)
1 [CoII(P1)] Ph Ph Me 64 (8a) (>95:5)
2 [CoII(P2)] Ph Ph Me 65 (8a) (>95:5)
3 [CoII(P3)] Ph Ph Me 65 (8a) (>95:5)
4 [CoII(P1)] Ph Ph PhCH2 62 (8b) (>90:10)
5 [CoII(P1)] Ph pClC6H4 Me 63 (8c) (>95:5)
6 [CoII(P1)] Ph pOMeC6H4 Me 73 (8d)(> 90:10)
7 [CoII(P1)] pMeC6H4 Ph Me 77 (8e) (>95:5)
8 [CoII(P1)] pClC6H4 Ph Me 62 (8f) (>95:5)
9 [CoII(P1)] pMeOC6H4 Ph Me 73 (8g) (>85:15)
10 [CoII(P1)] 2-napthyl Ph Me 67 (8h) (>95:5)
11 [CoII(P1)] PhCH = CH Ph Me 52 (8i) (>95:5)
[a]

Stoichiometry: N-tosylhydrazone:imine=1:2.

[b]

Isolated yields after column chromatography.