Literature DB >> 15760136

Cu(I)-catalyzed enantioselective [3 + 2] cycloaddition reaction of 1-alkylallenylsilane with alpha-imino ester: asymmetric synthesis of dehydroproline derivatives.

Kazunori Daidouji1, Kohei Fuchibe, Takahiko Akiyama.   

Abstract

[reaction: see text] The catalytic, enantioselective [3 + 2] cycloaddition reaction of 1-alkyl-substituted allenylsilanes with alpha-imino ester has been achieved by means of [Cu(MeCN)(4)]BF(4)/(R)-DM-SEGPHOS catalyst to afford silyl-substituted dehydroproline derivatives in high yields and enantioselectivities.

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Year:  2005        PMID: 15760136     DOI: 10.1021/ol047343c

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


  3 in total

1.  Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

2.  Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

3.  Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes.

Authors:  Stephen P Marsden; Pascal C Ducept
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883

  3 in total

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