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. Author manuscript; available in PMC: 2008 Aug 26.
Published in final edited form as: Chem Rev. 2007 May 27;107(6):2503–2545. doi: 10.1021/cr0509556

Table 9.

Catalyst comparison in the HKR of terminal epoxides with the oligomeric catalyst (Figure 8) and the standard (R,R)-(salen)Co(OAc).

graphic file with name nihms-63649-t0033.jpg
entry isolated product catalyst Co (mol%)a time (h)% yieldf (% ee)
epoxidesg
1b graphic file with name nihms-63649-t0034.jpg monomer
oligomer		 0.5
0.01		 18
11		 42(99)
45(99)
2c graphic file with name nihms-63649-t0035.jpg monomer
oligomer		 0.85
0.05		 68
24		 26(99)
36 (99)
3d graphic file with name nihms-63649-t0036.jpg monomer
oligomer		 0.8
0.08		 72
24		 44(99)
37(99)
4e graphic file with name nihms-63649-t0037.jpg monomer
oligomer		 2.0
0.1		 48
24		 41(99)
41(99)
diolsg
5d graphic file with name nihms-63649-t0038.jpg monomer
oligomer		 2.0
0.01		 24
1.5		 50(96)
40(97)
6d graphic file with name nihms-63649-t0039.jpg monomer
oligomer		 0.64
0.03		 20
4		 49(94)
46(97)
7d graphic file with name nihms-63649-t0040.jpg monomer
oligomer		 0.8
0.08		 12
4		 41(98)
43(96)
8d graphic file with name nihms-63649-t0041.jpg monomer
oligomer		 2.0
0.05		 20
18		 40(95)
49(95)
a

Loading on a Co basis relative to racemic epoxide.

b

Solvent-free.

c

Highly concentrated reaction using butyronitrile as solvent.

d

Highly concentrated reaction using 1:1 CH2Cl2: CH3CN as solvent.

e

Highly concentrated reaction using 1,2-hexanediol as solvent.

f

Isolated yield based on racemic epoxide.

g

For reactions in which resolved epoxide was targeted, 0.55-0.60 equiv H2O was used for the resolution. For recovery of diol, 0.45 equiv H2O was employed.