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. Author manuscript; available in PMC: 2011 Nov 10.
Published in final edited form as: J Am Chem Soc. 2010 Nov 10;132(44):15752–15765. doi: 10.1021/ja106837b

Table 3.

Achiral Lewis Base Survey with 34

graphic file with name nihms247258u3.jpg
entry acid Lewis base conv.,a %
3.5 h 24 h
1 none HMPA(S) 0 0
2 AcOH HMPA(S) 0 0
3 TFA HMPA(S) 73 95
4 MsOH HMPA(S) 100 -
5 TFA HMPA(Se) 21 72
6 TFA HMPA trace trace
7 TFA HMPT 45 85
8 TFA Ph3P(S) 100b -
9 TFA Cy3P(S) 100 -
10 TFA DMPU(S) 12 75
11 none none 0 0
12 TFA none trace trace
13 MsOH none 3 38
a

Conversion of 29 to 28f determined by 1H NMR spectroscopic analysis of the reaction mixture.

b

Complete conversion within 1.5 h.