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BINOLate - Magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2008)

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

卷 2008, 期 13, 页码 2248-2254

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.200701223

关键词

asymmetric catalysis; hetero-Diels - Alder reactions; nonlinear effect; magnesium; Danishefsky's diene; aldehydes

类别

Chemistry, Organic

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摘要

An efficient catalytic enantioselective hetero-Diels - Alder reaction of Danishefsky's diene with aldehydes using the magnesium binaphthoxide system has been developed, affording a variety of 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and with excellent ee values. The aggregation behavior and nonlinear effect of the catalytic system, as well as the remarkable stereoelectronic effects of ligands on the catalysis, have also been investigated. On the basis of the structure of the isolated reaction intermediate, the stereochemistry of the products, and the information attained from a study of the nonlinear effect, a plausible asymmetric induction model has been proposed. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

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