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. Author manuscript; available in PMC: 2011 Mar 17.
Published in final edited form as: J Am Chem Soc. 2010 Mar 17;132(10):3298–3300. doi: 10.1021/ja100502f

Table 1.

The (DHQD)2PHAL mediated halolactonization.

graphic file with name nihms-181443-f0001.jpg
Entry X+ Sourcea Solvent Additive °C % eeb
1 NBS CH2Cl2 - RT 22
2 NBS CH2Cl2 - −20 14
3 NBS CHCl3 - RT 35
4 NCS CH2Cl2 - RT 39
5 NCS CHCl3 - RT 65
6 NCS CHCl3 - −40 NRc
7 DCDMH CHCl3 - RT 71
8 DCDMH CHCl3 - −40 83
9 DCDMH CHCl3 PhCO2H −40 86
10 DCDMH CHCl3/Hex (1:1) - −40 86
11 DCDMH CHCl3/Hex (1:1) PhCO2H −40 89
12 DCDPH CHCl3/Hex (1:1) PhCO2H −40 89
a

X = Br for entries 1-3, and Cl for entries 4-12.

b

as judged by chiral HPLC or GC analysis.

c

NR = no reaction after 3 hours.