Literature DB >> 15281751

Memory of chirality in the transannular cyclization of cyclodecenyl radicals.

Jackline E Dalgard1, Scott D Rychnovsky.   

Abstract

The transannular cyclization of an enantioenriched cyclodecenyl radical proceeds in a 5-exo fashion to produce scalemic bicyclo[5.3.0]decanes. This cyclization is notable because it demonstrates chirality transfer through conformational memory of an unstabilized secondary radical. [reaction: see text]

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Year:  2004        PMID: 15281751     DOI: 10.1021/ol049038x

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


  4 in total

1.  Carboalumination of Seven-Membered-Ring trans-Alkenes.

Authors:  Margaret A Greene; Yudong Liu; Jillian R Sanzone; K A Woerpel
Journal:  Org Lett       Date:  2020-09-17       Impact factor: 6.005

2.  Approach for expanding triterpenoid complexity via divergent Norrish-Yang photocyclization.

Authors:  Vasily A Ignatenko; Gregory P Tochtrop
Journal:  J Org Chem       Date:  2013-04-11       Impact factor: 4.354

3.  Construction of bicyclic ring systems via a transannular SmI2-mediated ketone-olefin cyclization strategy.

Authors:  Gary A Molander; Barbara Czakó; Michael Rheam
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

4.  Total synthesis of rhazinilam: axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

  4 in total

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