Literature DB >> 11052083

Synthesis of cis,cis,cis-tetrasubstituted cyclobutanes. Trapping of tetrahedral intermediates in intramolecular nucleophilic addition

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Abstract

The intramolecular [2 + 2] photocycloaddition of bismaleimides leads to cage diimides 2. Nucleophilic addition on these compounds (NaBH4, RLi, or MeONa) gives rise to various diazatetracyclic 4 and 11 or oxadiazapentacyclic 3 "bowl shaped" alcohols. X-ray analyses of 3c and 11a provide definite structural data concerning these two highly functionalized compounds.

Entities:  

Year:  2000        PMID: 11052083     DOI: 10.1021/jo000361x

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

Review 2.  Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry.

Authors:  Christopher Hulme; Justin Dietrich
Journal:  Mol Divers       Date:  2009-02-11       Impact factor: 3.364

3.  Intramolecular thiomaleimide [2 + 2] photocycloadditions: stereoselective control for disulfide stapling and observation of excited state intermediates by transient absorption spectroscopy.

Authors:  Roshni Malde; Michael A Parkes; Michael Staniforth; Jack M Woolley; Vasilios G Stavros; Vijay Chudasama; Helen H Fielding; James R Baker
Journal:  Chem Sci       Date:  2022-01-28       Impact factor: 9.825

  3 in total

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