Nature Communications

Table 1 Optimization of the reaction conditions^a.

From: Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls


entry	R	cat (mol%)	solvent	T (°C)	time (h)	yield (%)^b	ee (%)^c
1	MOM	16a (10)	toluene	−50	72	45	57
2	MOM	16b (10)	toluene	−50	72	80	76
3	MOM	16c (10)	toluene	−50	72	87	86
4	Me	16c (10)	toluene	−50	72	91	45
5	Bn	16c (10)	toluene	−50	72	41	75
6	tBu	16c (10)	toluene	−50	72	46	72
7	Cy	16c (10)	toluene	−50	72	65	87
8	iPr	16c (10)	toluene	−50	72	95	90
9	3-Pen	16c (10)	toluene	−50	72	75	94
10	3-Pen	16c (10)	CH₂Cl₂	−50	76	97	96
11	3-Pen	16c (10)	CH₃CN	−25	76	81	86
12	3-Pen	16c (10)	CCl₄	−25	76	90	91
13	3-Pen	16c (10)	CHCl₃	−50	76	97	98
14	3-Pen	16c (10)	CHCl₃	−60	80	97	98
15	3-Pen	16c (10)	CHCl₃	−25	85	98	96
16	3-Pen	16c (10)	CHCl₃	0	85	96	95
17	3-Pen	16c (5)	CHCl₃	−50	82	97	97
18	3-Pen	16c (2)	CHCl₃	−50	82	96	97
19	3-Pen	16c (1)	CHCl₃	−50	82	80	96

^aReactions were carried out with 1-7a (0.24 mmol), 8a (0.2 mmol), catalyst (0.02 mmol) in solvent (2.0 mL) under N₂.
^bIsolated yield.
^cDetermined by HPLC analysis.

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