Table 2.

Asymmetric alcoholysis of cyclic anhydrides 1 with QD-MN and (DHQD)₂AQN^*

Entry	Substrate	Catalyst (mol%)	Alcohol (10 eq.)	Temp (°C)	Time	Yield †	ee ‡
1		QD-MN (10%)	CF3CH2OH	RT	5 h	91%	94%
2		(DHQD)2AQN (5%)	CF3CH2OH	RT	9 h	90%	90%
3		QD-MN (10%)	MeOH	RT	9 h	90%	90%
4		(DHQD)2 AQN (5%)	MeOH	RT	5 h	89%	94%
5		QD-MN (14%)	CF3CH2OH	RT	6 h	93%	95%
6		(DHQD)2AQN (7%)	CF3CH2OH	RT	5 h	96%	91%
7		QD-MN (14%)	MeOH	RT	8 h	91%	90%
8		(DHQD)2AQN (7%)	MeOH	RT	6 h	92%	94%
9		QD-MN (10%)	CF3CH2OH2	RT	7 h	96%	94%
10		(DHQD)2AQN (5%)	CF3CH2OH	RT	7 h	95%	89%
11		QD-MN (10%)	MeOH	RT	8 h	94%	87%
12		(DHQD)2AQN (5%)	MeOH	RT	4 h	95%	93%
13		QD-MN (20%)	MeOH	RT	36 h	88%	90%
14		(DHQD)2AQN (10%)	MeOH	RT	12 h	90%	88%
15		QD-MN (30%)	MeOH	−20	60 h	91%	95%
16		(DHQD)2AQN (15%)	MeOH	−20	120 h	88%	96%
17		QD-MN (40%)	MeOH	−20	48 h	87%	92%
18		(DHQD)2AQN (20%)	MeOH	−20	96 h	74%	92%

^*The reaction was carried out with 1 (0.02 M in diethyl ether) and R’OH [10 equivalent (eq.)] in the presence of catalyst.

^†Conversion was determined by ¹H NMR.

^‡See the SI Appendix for the determination of the ee value.