Nature Communications

Table 1 Optimization of positional isomerization of 1a^a

From: Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer



Entry	Solvent	Base	Yield (%)	Ee (%)	Es (%)
1	Toluene	DBU	78	87	91
2	Toluene	DBN	81	88	92
3	Mesitylene	DBN	70	87	91
4	THF	DBN	63	77	80
5	DME	DBN	85	70	73
6	DCE	DBN	77	50	52
7	1,4-Dioxane	DBN	83	90	94
8	MeOH	DBN	82	−50	52
9^b	MeOH	DABCO	81	−83	86
10^b	MeOH	Quinuclidine	73	−81	84
11	MeOH	MeONa	90	−79	82
12	MeCN	DABCO	50	−47	49
13	1,4-Dioxane	DABCO	40	−50	52
14	DME	DABCO	73	−52	54

^a Reaction conditions: Base (0.1 mmol, 0.1 mmol/mL) was rapidly added to 1a (0.1 mmol) in solvent (5 mL) at room temperature (rt) for 5 min.
^b Base (0.025 mmol, 0.1 mmol/mL) was rapidly added to 1a (0.1 mmol) in solvent (5 mL) at room temperature for 5 min. Isolated yield, the ee values were determined by chiral HPLC.

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