Literature DB >> 12203636

Formal enantioselective Michael addition with umpolung of reactivity.

E Hupe1, P Knochel.   

Abstract

By a sequence comprising asymmetric hydroboration, boron-zinc exchange, and transmetalation with copper, allylations, alkynylations, and allenylations of unsaturated ketals or acetals can be performed with good enantioselectivities (see scheme, (-)-IpcBH2 =(-)-isopinocampheylborane, TMS=Me3 Si). The products correspond to a formal Michael addition with inversion of polarity.
Copyright © 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Michael addition; asymmetric synthesis; hydroboration; umpolung; zinc

Year:  2001        PMID: 12203636     DOI: 10.1002/1521-3773(20010817)40:16<3022::AID-ANIE3022>3.0.CO;2-W

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  1 in total

1.  An Ionic Diels-Alder Route to cis-Fused Octalins Containing an All-Carbon Quaternary Stereocenter in an Angular Position.

Authors:  Jun Hee Lee; Woo Han Kim; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2010-03-03       Impact factor: 2.415

  1 in total

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