Efficient diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species

Reductive coupling reaction of aromatic and aliphatic aldehydes proceeded under mild conditions to give the corresponding pinacols in moderate to high yields and dl-diastereoselectivities by using combinations of either low valent titanium(II) bromide and copper or titanium(IV) iodide and copper in...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 13; pp. 2499 - 2506
Main Authors Mukaiyama, Teruaki, Yoshimura, Naritoshi, Igarashi, Koji, Kagayama, Akifumi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.03.2001
Elsevier
Subjects
aldehydes
Chemistry
Chemistry, Organic
coupling reactions
diastereoselection
diols
low valent titanium species
Physical Sciences
Science & Technology
low valent titanium species
aldehydes
diols
diastereoselection
coupling reactions
REAGENTS
CARBONYL-COMPOUNDS
ZINC
ALCOHOLS
KETONES
STEREOSELECTIVE PINACOLIZATION
CHEMISTRY
OLEFINS
MCMURRY REACTION
CHLORIDE
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Summary:Reductive coupling reaction of aromatic and aliphatic aldehydes proceeded under mild conditions to give the corresponding pinacols in moderate to high yields and dl-diastereoselectivities by using combinations of either low valent titanium(II) bromide and copper or titanium(IV) iodide and copper in a mixed solvent of dichloromethane and pivalonitrile. In the case of using titanium(IV) iodide and copper, pinacols were obtained in good to high yields with moderate to high diastereoselectivities irrespective of the number of substitutuents at α-position of aliphatic aldehydes. Low valent Ti: TiBr 2–Cu and TiI 4–2Cu good to high yields and dl-diastereoselectivities.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00074-6