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. Author manuscript; available in PMC: 2010 May 1.
Published in final edited form as: Nat Chem. 2009 Nov 1;1(8):630–634. doi: 10.1038/nchem.410

Table 1.

Selected data from sulfonylation catalyst screen.a

graphic file with name nihms145800u1.jpg
Entry Catalyst Temp. i+1 i+2 i+3 i+4 erb
1 3 23 °C Hyp(But) Sp5 Tyr(But) Phe 67.5:32.5
2 4 23 °C Hyp(But) Sp5 Leu Phe 84.5:15.5
3 5 23 °C Hyp(But) Aib Leu Phe 83.5:16.5
4 6 23 °C Pro Aib Leu Phe 76.5:23.5
5 4 0 °C Hyp(But) Sp5 Leu Phe 89.0:11.0
6 5 0 °C Hyp(But) Aib Leu Phe 87.0:13.0
7 7 0 °C Hyp(But) D-Val Leu Phe 92.5:7.5
8 8 0 °C Hyp(But) Val Leu Phe 60.0:40.0
9 9 0 °C Hyp(But) Sp5 Leu D-Phe 91.5:8.5
10 10 0 °C Hyp(But) Sp5 Leu ----- 97.0:3.0
11 11 0 °C Hyp(But) D-Val Leu ----- 95.5:4.5
a

Reactions were run with 1.0 equiv 2,4,6-tribenzyl-myo-inositol (1) and 1.0 equiv 4-nitrobenzenesulfonyl chloride. Reactions were run under a common set of conditions, and conversions were found to be approximately 10%, with some variation. The issue of secondary kinetic resolution was addressed subsequently (vide infra).

b

All enantiomer ratios were measured using chiral HPLC.