Sample reactions
intermediate structure intermediate structure
(CO2H)2, i-Pr2NLi
THF
-70 °C, 2 h
"Mixture of isomers."
intermediate structure
intermediate structure
NaOH
H2O, THF
RT
"Mixture of isomers."
intermediate structure
intermediate structure
NaOH
THF
RT
intermediate structure
intermediate structure
Me2S, O3, TsOH
EtOAc
90%
intermediate structure
intermediate structure
D-Proline
MeCN
RT
"Also isolated was the C6-epimer (50:50 dr). Both diastereoisomers were obtained as an enantioenriched mixture (36 % ee)."
intermediate structure
intermediate structure intermediate structure
MesLi
THF
-50 °C
intermediate structure
intermediate structure
EtCOSt-Bu, i-Pr2NLi
THF
-110 °C, , 85%
intermediate structure
intermediate structure
Cp2ZrCl2, EtCO2Me, i-Pr2NLi
THF
-78 °C to RT, 2 h, 60%
intermediate structure
intermediate structure
EtCO2t-Bu, i-Pr2NLi
HMPA, THF
-78 to -30 °C, 12 h, 60%
intermediate structure
intermediate structure intermediate structure
MeLi, MgBr2.OEt2
Et2O
-5 °C to RT, 70 min, 65%
intermediate structure
intermediate structure intermediate structure
NaOAc
THF
intermediate structure
intermediate structure intermediate structure
i-Pr2NMgBr
THF
-23 °C to RT, 2.5 h
intermediate structure
intermediate structure
CuI, MeLi
Et2O
-78 °C to RT, ON, 97%
intermediate structure
intermediate structure
DMAP, ClCO2CH2CCl3
CH2Cl2
RT, 42 h, 62%
intermediate structure
intermediate structure
i-Pr2NLi, i-PrCO2Me
Et2O
-78 °C, , 65%
"Also isolated was the C3-epimer (20 % yield)."
intermediate structure
intermediate structure
NaOMe
MeOH, THF
0 °C, , 90%
"Also isolated was the C4-epimer (8 % yield)."
intermediate structure
intermediate structure intermediate structure
i-Pr2NEt, PhBCl2
CH2Cl2
-78 to 0 °C, 2.5 h, 66%
intermediate structure
intermediate structure
DBU, DMSO, (CF3CO)2O
CH2Cl2
-78 °C to RT, 21 h
intermediate structure
intermediate structure
NaOMe
MeOH
70 °C, 2 h, 49% (2 steps)
intermediate structure
intermediate structure
TMS2NLi, ZnBr2, MeCHO
Et2O, THF
-78 to 0 °C, 2 h, 71%
intermediate structure
intermediate structure
i-Pr2NLi, LiBr, MeCO2t-Bu
Et2O
-78 °C, 90 min, 91%
intermediate structure
intermediate structure
KOH
MeOH
2.5 d, 26%
"The yield was 61 % brsm."
intermediate structure
intermediate structure intermediate structure
i-Pr2NEt, n-Bu2BOTf
CH2Cl2
-78 °C to RT, 2 h, 100%
intermediate structure
intermediate structure
i-Pr2NLi, MeCHO
HMPA, THF
-78 °C, 4.5 h, 96%
intermediate structure
intermediate structure intermediate structure
i-Pr2NEt, TiCl4
CH2Cl2
-78 °C to RT, 3.5 h, 64%
intermediate structure
intermediate structure
HCl
Acetone, H2O
RT, 3 d, 79% (2 steps)
intermediate structure
intermediate structure
HCl
H2O, THF
RT, , 71%
intermediate structure
intermediate structure
Me2CuLi
Et2O
-20 °C, 40 min, 96%
intermediate structure
intermediate structure intermediate structure
i-Pr2NLi, CdCl2
THF
-40 to 0 °C, 2.5 h, 73%
intermediate structure
intermediate structure
HCl
Acetone, H2O
RT, 60 min
intermediate structure
intermediate structure
HCl
H2O, THF
RT, 7 d, 86%
intermediate structure
intermediate structure
CH2O, i-Pr2NLi
THF
-23 °C, 80 min, 60%
intermediate structure
intermediate structure intermediate structure
TMS2NLi
THF
-78 °C, 55 min
intermediate structure
intermediate structure
i-Pr2NEt, TiCl4, TMSCl
CH2Cl2
0 °C, 20 min, 85%
intermediate structure
intermediate structure
HCl
Acetone, H2O
RT, 3 d, 72% (2 steps)
intermediate structure
intermediate structure intermediate structure
i-Pr2NLi
THF
-78 to 50 °C, 5 h
intermediate structure
intermediate structure intermediate structure
i-Pr2NLi, HMPA
THF
-78 °C, 20 min, 80%
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
110 °C, 2 h, 49% (2 steps)
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
110 °C, 2 h, 49% (2 steps)
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
110 °C, 2 h, 42% (4 steps)
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
110 °C, 2 h, 42% (2 steps)
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
110 °C, , 65%
intermediate structure
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 69%
intermediate structure
intermediate structure
HCl
H2O, THF
40 °C, 24 h, 84% (2 steps)
intermediate structure
intermediate structure intermediate structure
KOH
MeOH
RT, 30 min, 85%
intermediate structure