Heteroatom-directed. pi.-facial diastereoselection in Diels-Alder cycloadditions of plane-nonsymmetric cyclopentadienes

JB Macaulay, AG Fallis

Index: Macaulay; Fallis Journal of the American Chemical Society, 1990 , vol. 112, # 3 p. 1136 - 1144

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Citation Number: 121

Abstract

Abstract: The synthesis of a series of pentamethylcyclopentadienes bearing stereogenic C-5 heteroatom substituents and their reactions in [4+ 21 cycloadditions with maleic anhydride and/or N-phenylmaleimide are described. Cyclopentadienes (13, 14, 6, 7, and 1) containing the substituents OH, OCH,, NH,, NHAc, and CI reacted to form syn adducts preferentially. In contrast, with compound 8 (SH) only slight syn discrimination was observed, while the ...

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