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. 2015 Jul 3;11:1112–1122. doi: 10.3762/bjoc.11.125

Table 2.

Deprotection and alkylation of cyanoethyl-protected thiol moieties on MPTTFs using CsOH·H2O or DBU.

Substrate (R1) RX Product Base and conditions % Yield

4b (SEt) 20-I Inline graphic
4i
CsOH·H2O, THF, MeOH, rt, 16 h 92 (lit. 88 [45])
DBU, THF, reflux, 20 h 90
4a (SMe) 20-I Inline graphic
4j
CsOH·H2O, THF, MeOH, rt, 2.5 h 87
DBU, THF,
reflux, 18 h
91
4a (SMe) 21-Br graphic file with name Beilstein_J_Org_Chem-11-1112-i024.jpg CsOH·H2O, THF, MeOH, rt, 20 h 53
4a (SMe) 21-I DBU, THF,
reflux, 17 h
93
4a (SMe) 22-I graphic file with name Beilstein_J_Org_Chem-11-1112-i025.jpg CsOH·H2O, THF, MeOH, rt, 18 h 88
DBU, THF,
reflux, 3 d
92