Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides

Institution:	1. Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland;2. Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland;1. Institute of Microelectronics, Tsinghua National Laboratory for Information Science and Technology (TNList), Tsinghua University, Beijing 100084, People׳s Republic of China;2. Institute for Advanced Materials, South China Normal University, Guangzhou 510000, People׳s Republic of China;3. State Key Laboratory of New Ceramic and Fine Processing, Tsinghua University, Beijing 100084, People׳s Republic of China;1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran;2. School of Chemistry, University of Melbourne, Victoria 3010, Australia

Abstract:	The asymmetric cyclopropanation of a vinylphosphonate using optically active sulfonium and selenonium ylides derived from (−)-menthol and (+)-limonene was developed. The ylides were generated in situ by the reaction of the corresponding sulfonium or selenonium salt in the presence of potassium carbonate or DBU as a base. The transfer of the CHPh and CHCO₂Et groups into the cyclopropane ring showed moderate diastereoselectivity and excellent enantioselectivity (up to 99:1) for the trans- and cis-products. The absolute configuration of phenyl cyclopropyl was assigned based on comparison to their tolyl analogues.

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