Table 3. Results of the Phenol Hydroxyethylation Cascade^a.

substrate	product	R	convb (ee) [%]	yieldd (ee) [%]
1a	5a	H	73 (92)	–
1b	5b	2-Cl	85 (83)	–
1e	5e	2-Me	12c (95)	–
1f	5f	2-F	91 (81)	84 (78)
1g	5g	2-Br	84 (87)	58 (88)
1i	5i	3-F	80 (87)	72 (85)
1j	5j	3-Cl	36 (95)	29 (92)

^aReaction conditions analytical scale: Lyophilized E. coli whole cells containing the heterologously expressed TPL_Cf M379 V (10 mg mL^–1, 448 mU), TAL_Rs (40 mg mL^–1, 35 mU), FDC_Es wt (2 mg mL^–1, 3.2 U), and purified FDC_Es V46E variant (100 μM, 1 mol %) in reaction buffer [potassium phosphate buffer (50 mM, pH 8.0), sodium pyruvate (92 mM), NH₄Cl (180 mM), and PLP (80 μM), pH adjusted to 8.0] with substrate phenol (10 mM, 50 μL of a 200 mM stock in ⁱPrOH, 5% v/v). Incubation at 30 °C and 850 rpm for 24 h.

^bHPLC conversion: the corresponding vinylphenol 4 was detected as the major remaining intermediate.

^cPhenol 1e and tyrosine 2e were detected as major constituents.

^dIsolated yield after column chromatography.