Literature DB >> 12919019

Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4.

José Barluenga1, Mónica Alvarez-Pérez, Félix Rodríguez, Fracisco J Fañanás, José A Cuesta, Santiago García-Granda.   

Abstract

Acetonides 1, easily obtained from simple terpenes, react with bispyridine iodonium (I) tetrafluoroborate (Ipy(2)BF(4)) and tetrafluoroboric acid in the presence of nucleophiles to give the corresponding adducts 2 with complete regio and diastereofacial control. Acetonides 1 containing a properly located phenyl or benzyloxy group easily undergo iodocyclization to furnish compounds 3 and 4.

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Year:  2003        PMID: 12919019     DOI: 10.1021/jo034517f

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


  2 in total

1.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

2.  Aruncin B: Synthetic Studies, Structural Reassignment and Biological Evaluation.

Authors:  Aubert Ribaucourt; Christopher Towers; Laia Josa-Culleré; Frances Willenbrock; Amber L Thompson; David M Hodgson
Journal:  Chemistry       Date:  2017-10-30       Impact factor: 5.236

  2 in total

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