Asymmetric Diels–Alder reactions between chiral sugar nitroalkenes and 1-O-substituted buta-1,3-dienes. Synthesis and reactivity of new cyclohexenyl derivatives
作者： José A. Serrano , Luis E. Cáceres , Emilio Román
DOI: 10.1039/P19950001863
关键词: Reactivity (chemistry) 、 Regioselectivity 、 Chemistry 、 Diels alder 、 Sugar 、 Organic chemistry
摘要: Uncatalysed Diels–Alder reactions between 1-(trimethylsiloxy)- or 1-acetoxy-buta-1,3-diene and sugar-derived nitroalkenes having D-galacto D-manno configurations proceeded with complete regioselectivity. Diastereofacial specificity was also the dienophile, whereas it only moderate D-manno. With 1-acetoxybuta-1,3-diene, interaction reactants took place exclusively in endo mode. Starting from cycloadducts, a series of highly functionalised chiral compounds have been prepared, their conformations stereochemistries being investigated.
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sci-hub.se 参考文章(25)
Cycloaddition reactions in carbohydrate chemistry American Chemical Society. ,(1992) , 10.1021/BK-1992-0494
David Ginsburg, Tetrahedron report number 149 Tetrahedron. ,vol. 39, pp. 2095- 2135 ,(1983) , 10.1016/S0040-4020(01)91928-3
Richard W. Franck, S. Argade, C.S. Subramaniam, Denise M. Frechet, The face selectivity directed by an allylic group of a diene in the diels-alder reaction is reversed from that of a dienophile Tetrahedron Letters. ,vol. 26, pp. 3187- 3190 ,(1985) , 10.1016/S0040-4039(00)98148-6
S. D. Kahn, W. J. Hehre, Modeling chemical reactivity. 5. Facial selectivity in Diels-Alder cycloadditions Journal of the American Chemical Society. ,vol. 109, pp. 663- 666 ,(1987) , 10.1021/JA00237A004
Tony K.M. Shing, Yu-xin Cui, Ying Tang, (−)-Quinic acid in organic synthesis. 3. Stereocontrolled syntheses of pseudo-α-d-glucopyranose and pseudo-α-d-mannopyranose. Tetrahedron. ,vol. 48, pp. 2349- 2358 ,(1992) , 10.1016/S0040-4020(01)88756-1
V. VanRheenen, R.C. Kelly, D.Y. Cha, An improved catalytic OsO4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant Tetrahedron Letters. ,vol. 17, pp. 1973- 1976 ,(1976) , 10.1016/S0040-4039(00)78093-2
Noboru Ono, Hideyoshi Miyake, Akio Kamimura, Aritsune Kaji, Regioselective Diels–Alder reactions. The nitro group as a regiochemical control element Journal of The Chemical Society-perkin Transactions 1. pp. 1929- 1935 ,(1987) , 10.1039/P19870001929
Samuel Danishefsky, Michael P. Prisbylla, Steven Hiner, The use of trans-methyl .beta.-nitroacrylate in Diels-Alder reactions Journal of the American Chemical Society. ,vol. 100, pp. 2918- 2920 ,(1978) , 10.1021/JA00477A071
E.Roman Galan, Derek J. Hodgson, Yoshinobu Yokomori, Ernest L. Eliel, M.Bueno Martinez, Juan A.Serrano Blazquez, Synthesis and structural study of 5-nitro-6-(penta-O-acetylpentitol-1-yl)norbornenes Carbohydrate Research. ,vol. 180, pp. 263- 276 ,(1988) , 10.1016/0008-6215(88)80083-1
H.J. Koch, A.S. Perlin, Synthesis and 13C N.M.R. spectrum of D-glucose-3-d. bond-polarization differences between the anomers of D-glucose Carbohydrate Research. ,vol. 15, pp. 403- 410 ,(1970) , 10.1016/S0008-6215(00)80457-7