5.17 Reduction: Pinacol Coupling

J. Inanaga, Hiroshi Furuno

Research output: Chapter in Book/Report/Conference proceedingChapter

2 Citations (Scopus)


The pinacol coupling reaction, a reductive coupling reaction of carbonyl compounds that proceeds through the formation of ketyl radical intermediates, affords the corresponding 1,2-diols in one step. Chirality of the vicinal stereogenic centers that are formed can be induced or controlled by (1) chiral substrates with center-, axial-, or planar-chiralities or substrates modified by chiral auxiliaries, (2) chiral reducing agents such as low-valent metal complexes with chiral modifiers, or (3) chiral catalysts like transition metal complexes bearing chiral ligands, the low-valent species of which can be recycled in the presence of the appropriate coreductants. Thus, a variety of chiral and nonracemic (i.e., optically active) 1,2-diols were produced through the highly stereoselective pinacol coupling reactions performed either in an inter- or intramolecular way. The reductive homocoupling of imines (imino-pinacol coupling) and the carbonyl-imine heteropinacol coupling also proceeded to give the corresponding 1,2-diamines and 1,2-aminoalcohols, respectively, in high stereoselectivities under certain conditions. Some applications to the synthesis of biologically interesting organic molecules are also presented.

Original languageEnglish
Title of host publicationComprehensive Chirality
PublisherElsevier Ltd
Number of pages22
ISBN (Print)9780080951683
Publication statusPublished - Sep 1 2012

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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    Inanaga, J., & Furuno, H. (2012). 5.17 Reduction: Pinacol Coupling. In Comprehensive Chirality (Vol. 5, pp. 399-420). Elsevier Ltd. https://doi.org/10.1016/B978-0-08-095167-6.00519-X