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 |
![]() 4i |
CsOH·H2O, THF, MeOH, rt, 16 h | 92 (lit. 88 [45]) |
DBU, THF, reflux, 20 h | 90 | |||
4a (SMe) | 20-I |
![]() 4j |
CsOH·H2O, THF, MeOH, rt, 2.5 h | 87 |
DBU, THF, reflux, 18 h |
91 | |||
4a (SMe) | 21-Br | ![]() |
CsOH·H2O, THF, MeOH, rt, 20 h | 53 |
4a (SMe) | 21-I | DBU, THF, reflux, 17 h |
93 | |
4a (SMe) | 22-I | ![]() |
CsOH·H2O, THF, MeOH, rt, 18 h | 88 |
DBU, THF, reflux, 3 d |
92 |