Fig. 4: Multicomponent stereoretentive enantioconvergent reactions.
a, Enantioconvergent reaction starting from racemic tetrahydroisoquinoline 11 using a Bode-type acylating reagent 9. Et3N, triethylamine; THF, tetrahydrofuran. b, Enantioconvergent synthesis of α-aminoamide 15 from racemic primary amine 13 using a lipase biocatalyst and ethyl chloroacetate as the linker. EtOH, ethanol; MS, molecular sieve. c, Enantioconvergent synthesis starting from racemic secondary alcohol 17 using organocatalyst 18 and 2,2-dimethylglutaric anhydride 16 as the linker. HPLC chromatograms of the products (12, 15 and 20) are shown in black and are overlaid with chromatograms of their statistical stereoisomeric mixtures (that is, d.r. 1:1, 0% e.e.) in grey. ae.e. values are estimates assuming 50% conversion (s = 28); for full details, see section 3 of the Supplementary Information.
