Asymmetric Diels–Alder reactions. Part 3. Influence of butadiene structure upon the diastereofacial reactivity of (E)-1-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-dienes
Asymmetric Diels–Alder reactions. Part 3. Influence of butadiene structure upon the diastereofacial reactivity of (E)-1-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-dienes
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不对称狄尔斯-阿尔德反应第 3 部分。丁二烯结构对 (E)-1-(2′,3′,4′,6′-四-O-乙酰基-β-D-吡喃葡萄糖氧基)buta 的非对映反应性的影响。 -1,3-二烯
DOI：
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发表时间：
1989
期刊：
影响因子：
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通讯作者：
R. J. Stoodley
中科院分区：
文献类型：
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作者：
D. Larsen;R. J. Stoodley
(E)-1-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖氧基)丁-1,3-二烯(1c)、其3-甲基衍生物(1d)、其2,3-二甲基衍生物(1e)、其(3Z)-4-乙酰氧基-3-(叔丁基二甲基甲硅烷氧基)衍生物(1f)、其3-(叔丁基二甲基甲硅烷氧基)衍生物(1g)及其(3Z)-3-(叔丁基二甲基甲硅烷氧基)-2,4-二甲基衍生物(1h)已被制备，并评估了它们对N-苯基马来酰亚胺和四氰乙烯的非立体面反应性。在环境温度下，在苯中使用前二烯体，二烯（1c，d，f，g）得到约。 87：环加合物对(2c)和(3c)、(2d)和(3d)、(2f)和(3f)以及(2g)和(3g)的13种混合物；然而，二烯（1e，h）仅提供环加合物（2e，h）。在环境温度下，在苯中与四氰乙烯反应，前述二烯反应得到环加合物的混合物，范围从二烯(1c)情况下环加合物(6c)和(7c)的69:31混合物到二烯(1h)情况下环加合物(6h)和(7h)的89:11混合物。
(E)-1-(2′,3′,4′,6′-Tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-diene (1c), its 3-methyl derivative (1d), its 2,3-dimethyl derivative (1e), its (3Z)-4-acetoxy-3-(t-butyldimethylsilyloxy) derivative (1f), its 3-(t-butyldimethylsilyloxy) derivative (1g), and its (3Z)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl derivative (1h) have been prepared and their diastereofacial reactivities towards N-phenylmaleimide and tetracyanoethylene assessed. With the former dienophile in benzene at ambient temperature, the dienes (1c, d, f, g) gave ca. 87 : 13 mixtures of the cycloadduct pairs (2c) and (3c), (2d) and (3d), (2f) and (3f), and (2g) and (3g); however, the dienes (1e, h) afforded only the cycloadducts (2e, h). With tetracyanoethylene in benzene at ambient temperature, the aforecited dienes reacted to give mixtures of cycloadducts, ranging from a 69 : 31 mixture of the cycloadducts (6c) and (7c) in the case of the diene (1c) to an 89 : 11 mixture of the cycloadducts (6h) and (7h) in the case of the diene (1h).