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Ruthenium catalyzed C-C bond formation via transfer hydrogenation: branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes.

Authors
  • Ngai, Ming-Yu
  • Skucas, Eduardas
  • Krische, Michael J
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jul 03, 2008
Volume
10
Issue
13
Pages
2705–2708
Identifiers
DOI: 10.1021/ol800836v
PMID: 18533665
Source
Medline
License
Unknown

Abstract

Under the conditions of ruthenium-catalyzed transfer hydrogenation employing 2-propanol as the terminal reductant, 1,1-disubstituted allenes 1a- h engage in reductive coupling to paraformaldehyde to furnish homoallylic alcohols 2a- h. Under identical transfer hydrogenation conditions, 1,1-disubstituted allenes engage in reductive coupling to aldehydes 3a- f to furnish homoallylic alcohols 4a- n. In all cases, reductive coupling occurs with branched regioselectivity to deliver homoallylic alcohols bearing all-carbon quaternary centers.

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