An Efficient Stereoselective Synthesis of 4,5-trans-l,5-cis-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters

Shengming Ma; Lianghua Lu

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An Efficient Stereoselective Synthesis of 4,5-trans-l,5-cis-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters

机译：通过亚炔基环丙基酯的碘内酯化高效立体选择性合成4,5-反-1,5-顺-3-氧杂双环[3.1.0]己-2-酮

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A highly Stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH_3CN to afford 4,5-trans-l,5-cis-3-oxabicyclo-[3.1.0]hexane-2-ones is described.The reaction is very general,accommodating a wide range of substituents.A plausible mechanism that explains the essential role of water in this reaction is proposed.

机译：描述了在CH_3CN水溶液中用碘或N-碘琥珀酰亚胺（NIS）对亚烷基环丙基酯进行高度立体选择性的碘内酯化，得到4,5-反式-1,5-顺式-3-氧杂双环-[3.1.0]己烷-2-酮。该反应非常普遍，可容纳广泛的取代基。提出了一个合理的机理来解释水在该反应中的重要作用。

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来源
《The Journal of Organic Chemistry》 |2005年第19期|p.7629-7633|共5页
作者
Shengming Ma; Lianghua Lu;
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作者单位

State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,354 Fenglin Road,Shanghai 200032,People's Republic of China;

State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,354 Fenglin Road,Shanghai 200032,People's Republic of China;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类有机化学;
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入库时间 2022-08-18 00:03:12

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7. An Efficient Stereoselective Synthesis of 4, 5-trans-1, 5-cis-3-Oxabicyclo3.1.0hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters [O] . -1

机译：通过碘酰丁二酰酯的碘化碘化，有效的立体选择性合成4,5-Trans-1,5-CIS-3-Oxabidclo 3.1.0己酸-2-二甲酰胺

An Efficient Stereoselective Synthesis of 4,5-trans-l,5-cis-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters

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