Literature DB >> 11009391

Investigation of a dialkylation approach for enantioselective construction of vicinal quaternary stereocenters.

S B Hoyt1, L E Overman.   

Abstract

A detailed study of the dialkylation of dianions derived from dihydroisoindigo 1 with enantiopure ditriflate 2 is reported. The LHMDS-mediated process has been optimized to give C(2)-symmetric product 3 with high selectivity (C(2) selectivity 3:5 = 100:1; C(2):C(1) selectivity = 8:1). Stereoselection in the C(2) manifold is determined in both the bimolecular and intramolecular alkylation steps.

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Year:  2000        PMID： 11009391     DOI： 10.1021/ol006494m

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


  2 in total

1.  A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.

Authors:  J Michael Ellis; Larry E Overman; Huw R Tanner; Jocelyn Wang
Journal:  J Org Chem       Date:  2008-10-15       Impact factor: 4.354

Review 2.  Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors:  Emily A Peterson; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205
  2 in total

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