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- W2086136306 abstract "Chiral 1-phosphonodienes bearing a bicyclic (R,R)-1,3,2-dioxaphospholane or a (R,R)-1,3,2-diazaphospholidine auxiliary are potent dienes for asymmetric hetero Diels-Alder reactions. Their reactivity towards model nitroso and azodicarboxylate dienophiles has been studied by means of theoretical chemistry at the B3LYP/6-31G** level. This model, taking solvent effects into account, allowed us to identify parameters governing the stereoselectivity of this reaction. Our study emphasizes a synergy effect when increasing the steric hindrance of substituents of both partners. This led us to predict high levels of diastereoselectivity for one diene. Accordingly, we have hereby illustrated a convenient and original synthesis of this diene and its cycloadditions with commercially available nitroso and azodicarboxylate dienophiles. (C) 2009 Elsevier Ltd All rights reserved." @default.
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- W2086136306 date "2010-02-01" @default.
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- W2086136306 title "Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels–Alder cycloadditions with nitroso and azodicarboxylate dienophiles" @default.
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- W2086136306 doi "https://doi.org/10.1016/j.tetlet.2009.12.063" @default.
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