MATEO: intermolecular α-amidoalkylation theoretical enantioselectivity optimization. Online tool for selection and design of chiral catalysts and products

Table 9 HPTML study of new enantioselective intermolecular α-amidoalkylation reactions

Reaction inputs^a		Reaction features^b	New reactions (Table 8)
Reaction inputs^a		Reaction features^b	1	2	3	4	5	6	7	8
Reactants		Nuc	3a	3a	3a	3a	3b	3c	3d	3e
Reactants		Cat	4a	4b	4c	4d	4a	4a	4a	4a
Input conditions		Load (%)	20	20	20	20	20	20	20	20
		T (⁰C)	25	25	25	25	25	25	25	25
		T (h)	24	24	24	24	16	24	24	5
Heuristic	Data	ee_R (%)	Observed, Predicted, and Residual values
–	OD	Observed	93	0	26	65	11	67	52	54
H₁	OD	Predicted	66.0	29.7	64.1	25.1	− 90.5	74.9	61.8	42.4
		Residual	27.0	− 29.7	− 38.1	39.9	101.5	− 7.9	− 9.8	11.6
	ODMC	Predicted	91.1	0.3	64.1	25.1	12.1	66.6	50.8	52.1
		Residual	1.9	− 0.3	− 38.1	39.9	− 1.1	0.4	1.2	1.9
H₂	OD	Predicted	− 36.2	22.0	− 50.8	− 50.9	− 121.3	− 36.1	− 49.2	− 57.9
		Residual	129.2	− 22.0	76.8	115.9	132.3	103.1	101.2	111.9
	ODMC	Predicted	− 34.3	21.6	− 49.6	− 49.2	− 119.3	− 34.5	− 47.7	− 56.2
		Residual	127.3	− 21.6	75.6	114.2	130.3	101.5	99.7	110.2

^aOD Original Data, MC Monte Carlo, ODMC OD + MC enriched dataset. Nuc = Nucleophile, Cat = Catalyst, Load (%) Catalyst loading (%), the symbols 3a - 4d are Nuc and Cat, see scheme 4

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