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. Author manuscript; available in PMC: 2010 Jan 9.
Published in final edited form as: J Am Chem Soc. 2009 May 13;131(18):6383–6385. doi: 10.1021/ja9004909

Table 1.

Epoxy alcohol cyclizations with various additives.

graphic file with name nihms166088t1.jpg
entry X time (h) additive % conversiona 2:3a
1 O (1a) 33 none 58 (4) 11:1 (1)
2 O (1a) 33 CTABrb 67 (1) 12:1 (2)
3 O (1a) 33 LiCl (4M) 88 (2) 15:1 (1)
4 O (1a) 33 LiClO4 (4M) 73 (3) 12:1 (1)
5 O (1a) 33 pH 7 (1M)c 81 (2) 10:1 (1)
6 CH2 (1b) 2 none 80 (12) 1:1.3 (0.1)
7 CH2 (1b) 2 CTABrb 71 (7) 1:1 (0.2)
8 CH2 (1b) 2 LiCl (4M) 93 (4) 1:1.3 (0.1)
9 CH2 (1b) 2 LiClO4 (4M) 81 (2) 1:1.3 (0.1)
10 CH2 (1b) 2 pH 7 (1M)c 82 (6) 1:1.2 (0.3)
a

Average of three measurements; average error in parentheses.

b

cetyl trimethyl ammonium bromide, 2 equiv.

c

K2HPO4/KH2PO4 buffer.