Chemoenzymatic one-pot reactions with 2c and aromatic aldehydes 1a–1ea.
| ||
|---|---|---|
| Aldehyde | R | 4 Yieldb (ratio 1R,3S : 1S,3S) |
| 1a | CH2Ph | 4a 40% (1 : 1) |
| 1b | Ph | 4b 50% (3 : 1) |
| 1c | 4-ClC6H4 | 4c 25% (3 : 1) |
| 1d | 4-BrC6H4 | 4d 36% (3 : 1) |
| 1e | 2-BrC6H4 | 4e 77% (1 : 1) |
Reaction conditions: (i) 2b/2c and aldehydes (1 : 1.5) (other than 1 h with a ratio of 3 : 1), sodium ascorbate (3 equiv.), CnTYR lysates (10%, v/v) in 0.2 M KPi buffer/CH3CN (10%, v/v), pH 6.0, 37 °C, 18 h.
Yields were determined by analytical HPLC (against product standards). Diastereoselectivities were determined by HPLC and 1H NMR spectroscopy with assignment of the sterochemistry using NOEs (see ESI).30
