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Retentive Stereospecificity in Deoxygenation of Epoxides with Sn–Al or Si–Al Reagents
作者:Seijiro Matsubara、Tsuyoshi Nonaka、Yasuhiro Okuda、Shigekazu Kanemoto、Koichiro Oshima、Hitosi Nozaki
DOI:10.1246/bcsj.58.1480
日期:1985.5
Reaction of epoxides with [n-Bu3SnAlMe3]−Li+ affords β-oxido stannanes which collapse to alkene with overall retention of stereochemistry. The SN2 type ring opening of epoxides by tributylstannyl anion followed by anti elimination of Bu3Sn and OAl−Me3 groups explains the stereochemical results. The method can be successfully applied to hydroxy epoxides derived from (E)-2-nonen-1-ol. The deoxygenation of epoxides
环氧化物与 [n-Bu3SnAlMe3]-Li+ 的反应提供了 β-氧化锡烷,该锡烷会塌陷成烯烃,并保持立体化学的整体保留。三丁基甲锡烷基阴离子对环氧化物的 SN2 型开环,随后 Bu3Sn 和 OAl-Me3 基团的反消除解释了立体化学结果。该方法可成功应用于衍生自 (E)-2-nonen-1-ol 的羟基环氧化物。用 PhMe2SiAlEt2 对环氧化物进行脱氧还提供与环氧化物具有相同几何结构的烯烃。
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WEISEMANN, CLAUS;SCHMIDTBERG, GUNTHER;BRUNE, HANS-ALBERT, J. ORGANOMET. CHEM., 365,(1989) N, C. 403-412
作者:WEISEMANN, CLAUS、SCHMIDTBERG, GUNTHER、BRUNE, HANS-ALBERT
DOI:——
日期:——
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ZAVGORODNIJ, V. S.;ZUBOVA, T. P.;SIMIN, V. B.;PETROV, A. A., ZH. OBSHCH. XIMII, 1981, 51, N 9, 2048-2057
作者:ZAVGORODNIJ, V. S.、ZUBOVA, T. P.、SIMIN, V. B.、PETROV, A. A.
DOI:——
日期:——
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RUSSELL, G. A.;HEROLD, L. L., J. ORG. CHEM., 1985, 50, N 7, 1037-1040
作者:RUSSELL, G. A.、HEROLD, L. L.
DOI:——
日期:——
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Zavgorodnii, V. S.; Zubova, T. P.; Simin, V. B., Journal of general chemistry of the USSR, 1981, vol. 51, p. 1765 - 1773
作者:Zavgorodnii, V. S.、Zubova, T. P.、Simin, V. B.、Petrov, A. A.
DOI:——
日期:——