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. 2019 Mar 18;10(16):4515–4522. doi: 10.1039/c9sc00125e

Table 1. rDA studies of azabicycle-cysteine adducts.

Inline graphic
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.