Literature DB >> 16787071

Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.

Eric C Hansen1, Daesung Lee.   

Abstract

A novel mode of regiochemical control over the allylic [1,3]-transposition of silyloxy groups catalyzed by Re2O7 has been developed. This strategy relies on a cis-oriented vinyl boronate, generated from the Alder-ene reaction of homoallylic silyl ethers and alkynyl boronates, to trap out the allylic hydroxyl group. The resulting cyclic boronic acids are excellent partners for cross-coupling reactions. High chirality transfer is observed for the rearrangement of enantioenriched allylic silyl ethers.

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Year:  2006        PMID： 16787071      PMCID： PMC2528283          DOI： 10.1021/ja0620639

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

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5.  Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis.

Authors:  Christie Morrill; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

6.  Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes.

Authors:  Eric C Hansen; Daesung Lee
Journal:  J Am Chem Soc       Date:  2005-03-16       Impact factor: 15.419

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Authors:  Q Jean Zhou; Karin Worm; Roland E Dolle
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  7 in total
  5 in total

1.  Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.

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Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

2.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

3.  Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.

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Review 5.  Zampanolide and dactylolide: cytotoxic tubulin-assembly agents and promising anticancer leads.

Authors:  Qiao-Hong Chen; David G I Kingston
Journal:  Nat Prod Rep       Date:  2014-09       Impact factor: 13.423
  5 in total

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