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. Author manuscript; available in PMC: 2018 Aug 28.
Published in final edited form as: Angew Chem Int Ed Engl. 2007;46(37):7010–7014. doi: 10.1002/anie.200701280

Table 2.

Kinetic Resolutions with the CoIII-4a-OAc Catalyst

Epoxide Loading
(mol%)
Cond.[c] Isolated epoxide
(% yield, % ee, E-value)
Isolated diol
(% yield, % ee, E-value)
graphic file with name nihms-983018-t0013.jpg 1 A 70, 33 S, 11 26, 72 R,[c] 8
graphic file with name nihms-983018-t0014.jpg 1 A 44, 92 S, 20 56, 72 R,e19
graphic file with name nihms-983018-t0015.jpg 4 B 59, 55 (S), 16 39, 80 (R),[d] 15
graphic file with name nihms-983018-t0016.jpg 2 B 59, 53 (S), 13 37, 75 (R),[d] 11
graphic file with name nihms-983018-t0017.jpg 2 B 45, 93 R,[e] 25 55, 72 S,[e],[f] 17
graphic file with name nihms-983018-t0018.jpg 1 B 82, 17 S, 9 18, 80 R,[f] 11
graphic file with name nihms-983018-t0019.jpg 10 B 62, 28 R,[g] 3.5 37, 46 S,[e] 3.5
[a],[b]

as for Table 1;

[c]

Assigned by comparison of optical rot'n with that of the known R-diol (ref 25);

[d]-[f]

– see notes

[c]-[e]

, Table 1;

[g]

The sign of the optical rotation was found to differ with that reported [the S-epoxide is said to levorotatory (ref 24) but the R-epoxide was found to be levorotatory here]. To confirm the absolute stereochemistry, the R-epoxide was independently from S-glycidol.

[h]

note

[g]

, Table 1.