N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium in tetrahydrofuran
T=-78 - 20°C; one-pot reaction with aldehydes and ketones giving stereoselectively E-1,3-dienes, also with 3-diphenylphosphoryl-1-butene; Product distributionMechanism;
1: 1-tert-butyl-5-(prop-2-ene-1-sulfonyl)-1H-tetrazole With potassium hexamethylsilazane in ethylene glycol dimethyl ether
T=-60°C; Metallation; 0.5 h;
2: Decanaldehyde T=-60 - 20°C; Julia olefination; Title compound not separated from byproducts;
参考文献
Kocienski, Philip J.; Bell, Alan; Blakemore, Paul R.
Synlett, 2000 , # 3 p. 365 - 366
1: 1-phenyl-5-(prop-2'-ene-1'-sulfonyl)-1H-tetrazole With potassium hexamethylsilazane in ethylene glycol dimethyl ether
T=-60°C; Metallation; 0.5 h;
2: Decanaldehyde T=-60 - 20°C; Julia olefination; Title compound not separated from byproducts;
参考文献
Kocienski, Philip J.; Bell, Alan; Blakemore, Paul R.
Synlett, 2000 , # 3 p. 365 - 366
1: allyl phosphonic acid diethyl ester With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.25 h;
2: Decanaldehyde With N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane
T=-78 - 20°C; Horner-Wadsworth-Emmons reaction; 14 h; Title compound not separated from byproducts;
1: 87 percent / piperidinium acetate / dimethylsulfoxide / 100 °C
2: 82 percent / Na[(CH3OCH2CH2O)2]AlH2 / diethyl ether / 2 h / 25 °C
View Scheme
参考文献
Bikulova, L. M.; Verba, G. G.; Kamaev, F. G.; Abduvakhabov, A. A.
Chemistry of Natural Compounds, 1988 , vol. 24, # 5 p. 580 - 581
Khimiya Prirodnykh Soedinenii, 1988 , vol. 24, # 5 p. 682 - 683
