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Synthesis and applications of (1R, 5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions

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TETRAHEDRON-ASYMMETRY
卷 11, 期 13, 页码 2733-2739

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(00)00242-1

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A short asymmetric synthesis of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol 7 is described along with its application as a chiral auxiliary in various Diels-Alder reactions. The enantioselectivity of the Diels-Alder adducts ranged from 86-98% ee. The Diels-Alder adducts were easily removed from the chiral auxiliary and the latter was recyclized. The absolute and relative stereochemistry of 7 was determined from an X-ray crystal structure of the p-bromobenzoate derivative of 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

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