Nature Communications

Table 1 Optimizations of reaction conditions^a

From: Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization


Entry	CPA	Solv.	Yield of 3a (%)^b	Ee of 3a (%)^c
1	A1	Tol	91	85
2	A2	Tol	67	45
3	A3	Tol	63	73
4	A4	Tol	88	60
5	A5	Tol	79	73
6	A6	Tol	95	70
7	A7	Tol	85	40
8	A8	Tol	80	36
9	A9	Tol	91	97
10	A9	DCM	89	97
11	A9	Et₂O	47	97
12	A9	EtOAc	43	97
13	A9	THF	<5	ND
14 ^d	A9	DCM	88	97

^aReactions were performed with 1a (0.015 mmol), 2a (0.018 mmol) CPA catalyst (10 mol%) in solvent (0.5 mL) at 20 ^oC for 12 h. ^bIsolated yield. ^cEe values were determined by chiral HPLC analysis. ^dCPA A9 (1 mol%) was used, and the reaction time was extended to 24 h.

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