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. Author manuscript; available in PMC: 2010 Dec 2.
Published in final edited form as: J Am Chem Soc. 2009 Dec 2;131(47):17074–17075. doi: 10.1021/ja909030c

Table 1.

Optimization of reaction conditions.

graphic file with name nihms158995u2.jpg
entry X Y solvent time %conva %yielda erb drb
1c 10 -- MeOH 15 h 100 2 88:12 2.4:1
2 10 -- MeOH 15 h 74 8 92:8 2.7:1
3 10 20 MeOH 10 min 100 95 92:8 9.4:1
4 4 8 MeOH 30 min 100 87 92:8 9.6:1
5 4 8 THF 2 h 79 54 98:2 7.8:1
6 4 8 toluene 2 h 96 68 97:3 5.1:1
7 4 8 1:1 THF:toluene 5 h 100 67 97:3 6.7:1
8d 4 8 1:1 THF:toluene 2 h 99 80 98:2 8.9:1

Reactions run on 0.1 mmol scale with [2]=0.1 M.

a

Determined by GC analysis using an internal standard.

b

Determined by GC with a column equipped with a chiral stationary phase.

c

With 50 mg 3 Å MS and without KHCO3.

d

CuCl was used in place of CuCl2

d