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. Author manuscript; available in PMC: 2008 Sep 8.
Published in final edited form as: J Am Chem Soc. 2006 Jan 25;128(3):925–934. doi: 10.1021/ja056150x

Table 3.

3-Methyl-5-arylfuran enol carbonate rearrangement

graphic file with name nihms63193f13.jpg
Entry Substrate Solvent 45:46 a eemajor (%)
1b 44a CH2Cl2 3 : 2 75
2b 44b CH2Cl2 3 : 2 91
3 44c CH2Cl2 5 : 1 82
4 44c THF 10 : 1 90c
5 44c Et2O 11 : 1 83
6 44c toluene 10 : 1 74
7 44c t-amyl-OH 6 : 1 91
8d 44d CH2Cl2 1 : 4 63
9d 44d THF 1 : 4 74
10d 44d Et2O 1 : 4 90e
11d 44d toluene 1 : 4 83
12d 44d t-amyl-OH 1 : 4 50
a

ratio based on NMR assay, >95% conversion

b

1 mol% of catalyst 1

c

45: 83% yield 45; 46: 7% yield (80% ee)

d

reaction complete in 4 h

e

46: 75% yield; 45: 25% yield