Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8‐Oxabicyclo[3.2.1]octane Frameworks

• Toda, Yasunori

• Shimizu, Masahiro

• Iwai, Taichi

• Suga, Hiroyuki

書誌事項

タイトル別名

• Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8-Oxabicyclo[3.2.1]octane Frameworks

抄録

An efficient method for the preparation of a range of 8-oxabicyclo[3.2.1]octane derivatives including synthetic intermediates of natural products is described, in which triethylamine effectively catalyzes [5+2] cycloaddition reactions between oxidopyrylium ylides and alkenes. This method can be applied not only to intermolecular cycloadditions with various alkenes but also to intramolecular cycloadditions. The key finding is that the combined use of organic bases having appropriate basicity and oxidopyrylium ylide precursors bearing a suitable leaving group facilitates the base-assisted generation of oxidopyrylium ylides in a catalytic manner.

Article

ADVANCED SYNTHESIS & CATALYSIS.360(12):2377-2381(2018)

収録刊行物

• ADVANCED SYNTHESIS & CATALYSIS

  ADVANCED SYNTHESIS & CATALYSIS 360 (12), 2377-2381, 2018-06-15

  WILEY-V C H VERLAG GMBH

キーワード

• Cycloaddition
• Organic Base
• Base Catalysis
• Oxidopyrylium Ylide
• Alkenes

詳細情報

• CRID: 1050565163351019776
• NII論文ID: 120007099649
• NII書誌ID: AA11553845
• ISSN: 16154150
• ISSN: 16154169
• DOI: 10.1002/adsc.201800290
• HANDLE: 10091/00021870
• Web Site: https://soar-ir.repo.nii.ac.jp/records/21113
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.201800290
• Web Site: http://api.wiley.com/onlinelibrary/chorus/v1/articles/10.1002%2Fadsc.201800290
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.201800290
• 本文言語コード: en
• 資料種別: journal article
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