Literature DB >> 11348199

Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates.

C Schultz-Fademrecht1, B Wibbeling, R Fröhlich, D Hoppe.   

Abstract

[reaction: see text]. The alpha-deprotonation of alkynyl carbamates 3 with the chiral base (-)-sparteine (4)/n-butyllithium, transmetalation with ClTi(O(i)()Pr)3, and subsequent substitution with an aldehyde results in the formation of enantioenriched 4-hydroxyallenyl carbamates 11. Stereoselection is determined by dynamic resolution of the lithium/(-)-sparteine complexes by selective crystallization.

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Year:  2001        PMID： 11348199     DOI： 10.1021/ol0157104

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


  4 in total

1.  Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.

Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823

2.  Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

Authors:  Jennifer A Dabrowski; Fredrik Haeffner; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

3.  Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors:  Gary A Molander; Erin M Sommers; Sharon R Baker
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354

4.  Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Authors:  Yu-Long Hu; Zhe Wang; Hui Yang; Jie Chen; Zi-Bo Wu; Yibo Lei; Ling Zhou
Journal:  Chem Sci       Date:  2019-05-20       Impact factor: 9.825
  4 in total

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