有机化学习题福山组会题2012年05
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CO2Me CO2Me
2
1)
Ph O
O OEt
reflux N H 2) TsNHNH2 DME 0 ºC to reflux 80% (2 steps)
KOt-Bu toluene, reflux 60% dr = 3.5:1
HCl (gas) MeOH, rt 100%
Ph H
CO2Me NH•HCl
3
1) Co2(CO)8 CH2Cl2 rt, 92% BzO TMS 2) furan, EtAlCl2 CH2Cl2 –20 to 0 °C, 77% 1) I2, MeOH, rt 52% 2) n-BuLi THF, –78 °C 90% H OH
MeO
K. Tanino et al., Tetrahedron Lett., 52, 910 (2011)
Fukuyama Group - Group Meeting Problems 05/09/2012
1
O NaN3, MsOH, rt; aq. KOH 68% DPPA, Et3N toluene, rt; BnOH, reflux 87%
TfOH CH2Cl2, 0°C 79%
NH
Y. Iwabuchi et al., Synthesis, 3418 (2011)
2
MeO
Cr(CO)5
MeO MeO
OMe OMe
t-BuNC THF, rt 85%
1) TFA THF-H2O, rt 85% 2) MeOH, 100 ºC 92%
O O MeO
OMe NHt-Bu
neat, rt 98%
J. Barluenga et al., Chem. Eur. J., 8, 4149 (2002)
J. D. Winkler et al., J. Org. Chem., 63, 9628 (1998)
3Байду номын сангаас
O Me Me O O H Me hν DIBAL MeCN/acetone (9/1) Et2O, –60 °C; Me 0 to 15 °C AcOEt, H2O 98% monocyclic compound p-TsOH benzene reflux 50% (2 steps) dr = 3:2 H. Takeshita et al., Bull. Chem. Soc. Jpn., 66, 2694 (1993) O O Me Me
4
NaH N-methylaniline Adiponitrile THF, reflux 98% C6H7NO 4-chlorobutyronitrile K2CO3 DMF, 80 °C 65% NaH DME, reflux 25% N NH2 O
H.-J. Liu et al., Tetrahedron, 59, 1209 (2003) K. Sasaki et al., Tetrahedron Lett., 51, 903 (2010)
Fukuyama Group - Group Meeting Problems 05/23/2012
1
Cl O DMAD, i-Pr2NEt 1-Me-imidazole CH2Cl2, –10 °C to rt; H2O, rt 58%, Z/E = 79:21 Y. Wang et al., Org. Lett., 7, 2125 (2005)
4
O O O H Me3NO•2H2O 0 °C to rt 69% Co2(CO)8, MS4A toluene, rt; O K2CO3 MeOH 0 °C to rt 55% J. D. Winkler et al., Org. Lett., 7, 1489 (2005) O H
CO2Me