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. 2022 Dec 12;4(2):132–137. doi: 10.1039/d2cb00237j

Chemoenzymatic one-pot reactions with 2c and aromatic aldehydes 1a–1ea.

graphic file with name d2cb00237j-u2.jpg
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)
a

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.

b

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