Table 2.
Substrate scope of Mb(H64V,V68A)-mediated olefin cyclopropanation with diazoacetonitrile.[a]
 | |||||
|---|---|---|---|---|---|
| Entry | Product | Conv. (Yield) [b] |
TON | % de | % ee |
| 1 |  |
50% (44%) |
2080 | >99 | 96 |
| 2 |  |
99% (74%) |
4960 | 97 | 96 |
| 3 |  |
32% (31%) |
2420 | >99 | >99 |
| 4 |  |
77% (50%) |
3820 | >99 | >99 |
| 5 |  |
77% (66%) |
3820 | 98 | 97 |
| 6 |  |
98% (84%) |
4880 | >99 | 99 |
| 7 |  |
75% (66%) |
3730 | >99 | >99 |
| 8 |  |
65% (61%) |
2760 | 99 | 97 |
| 9 |  |
63% (61%) |
2550 | 84 | 85 |
| 10 |  |
87% (73%) |
3540 | >99 | 99 |
| 11 |  |
96% (61%) |
3810 | >99 | 76 |
| 12 |  |
90% (71%) |
3590 | >99 | 85 |
| 13 |  |
2% (nd) |
110 | 69 | >99 |
| 14 |  |
5% (nd) |
380 | 17 | 46 |
[a]
Reaction conditions: 30 mM olefin, Mb(H64V,V68A)-expressing E. coli (OD600 = 20) in KPi buffer (50 mM, pH 7), 20 mL-scale, RT, 5–12 hours. NaNO2 was slowly added over 30 min.
[b]
Product conversion as determined by SFC. Isolated yields are reported in brackets. Errors are within 15%.