5.17 Reduction: Pinacol Coupling

J. Inanaga, Hiroshi Furuno

Research output: Chapter in Book/Report/Conference proceedingChapter

2 Citations (Scopus)

Abstract

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
Pages399-420
Number of pages22
Volume5
ISBN (Print)9780080951683
DOIs
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