Literature DB >> 11440581

Kinetically controlled cross-metathesis reactions with high E-olefin selectivities.

F C Engelhardt1, M J Schmitt, R E Taylor.   

Abstract

[reaction: see text] Homoallylic alcohols with anti-allylic substituents display enhanced E-olefin selectivity in cross-metathesis (CM) reactions with allyltrimethylsilane. The high selectivity can be explained via a five-membered chelate intermediate in which the hydroxyl group of the homoallylic alcohol coordinates to the ruthenium metal center of Grubbs' catalyst.

Entities:  

Year:  2001        PMID： 11440581     DOI： 10.1021/ol016061z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

Authors:  Minoru Ikoma; Masato Oikawa; Martin B Gill; Geoffrey T Swanson; Ryuichi Sakai; Keiko Shimamoto; Makoto Sasaki
Journal:  European J Org Chem       Date:  2008-11

2.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

3.  New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand.

Authors:  Agnieszka Hryniewicka; Szymon Suchodolski; Agnieszka Wojtkielewicz; Jacek W Morzycki; Stanisław Witkowski
Journal:  Beilstein J Org Chem       Date:  2015-12-30       Impact factor: 2.883
  3 in total

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