Nature Communications

Table 1 Reaction optimization with 2-naphthylamine^a

From: Organocatalytic atroposelective construction of axially chiral arylquinones


entry	CPA	solvent	time (min)	yield (%)^b	ee (%)^c
1	(R)-CPA1	CH₂Cl₂	240	32	–4
2	(R)-CPA2	CH₂Cl₂	240	38	–36
3	(R)-CPA3	CH₂Cl₂	240	27	–51
4	(S)-CPA4	CH₂Cl₂	20	87	99
5	(R)-CPA5	CH₂Cl₂	20	85	99
6	(R)-CPA6	CH₂Cl₂	240	36	–83
7	(R)-CPA7	CH₂Cl₂	240	57	–47
8	(R)-CPA8	CH₂Cl₂	240	52	–30
9	(R)-CPA9	CH₂Cl₂	240	24	–28
10	(R)-CPA10	CH₂Cl₂	240	35	–14
11	(R)-CPA11	CH₂Cl₂	240	38	–42
12	(S)-CPA4	toluene	20	60	99
13	(S)-CPA4	CHCl₃	20	82	99
14	(S)-CPA4	EtOAc	20	43	68
15	(S)-CPA4	DCE	20	86	99
16	(S)-CPA4	ether	20	62	83
17^d	(S)-CPA4	CH₂Cl₂	20	86	99
18^e	(S)-CPA4	CH₂Cl₂	20	86	99

^aReaction conditions: 1a–1 (0.22 mmol), 2a–1 (0.10 mmol), solvent (2 mL) under Ar atmosphere, unless noted otherwise. ^bIsolated yields. ^cDetermined by HPLC analysis on a chiral stationary phase. ^dConducted with 5 mol% of CPA4. ^eConducted with 1 mol% of CPA4

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