Literature DB >> 19877630

Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates.

Daniel R Fandrick1, Jonathan T Reeves, Zhulin Tan, Heewon Lee, Jinhua J Song, Nathan K Yee, Chris H Senanayake.   

Abstract

The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.

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Year:  2009        PMID: 19877630     DOI: 10.1021/ol9022529

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


  1 in total

1.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

  1 in total

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