Table 1. rDA studies of azabicycle-cysteine adducts.
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Entry | Vinyl sulfone a | Azabicycle-Cys adduct | R | P | Solvent | Half-life |
1 | 1 | 2 | H | Boc | CDCl3 | 16.4 h |
2 | 5 | 6 b | Me | Boc | CDCl3 | <5 min |
3 | 7 | 8 | H | Ac | CDCl3 | 37 h c |
4 | 7 | 8 | H | Ac | DMSO-d6 | 59 h |
aSee ESI for details on the synthesis of vinyl sulfones 5 and 7.
bAzabicycle-cysteine adduct 6 was not observed because it decomposes directly to give 9 and N-Boc-2,5-dimethylpyrrole.
c t 1/2 = 40 h; CDCl3 is pre-neutralized with K2CO3.