5.17 Reduction

Pinacol Coupling

J. Inanaga, Hiroshi Furuno

研究成果: 著書/レポートタイプへの貢献

2 引用 (Scopus)

抄録

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.

元の言語英語
ホスト出版物のタイトルComprehensive Chirality
出版者Elsevier Ltd
ページ399-420
ページ数22
5
ISBN(印刷物)9780080951683
DOI
出版物ステータス出版済み - 9 1 2012

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Imines
Chirality
Coordination Complexes
Bearings (structural)
Stereoselectivity
Carbonyl compounds
Diamines
Reducing Agents
Substrates
Transition metals
Ligands
Catalysts
Molecules

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

これを引用

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

5.17 Reduction : Pinacol Coupling. / Inanaga, J.; Furuno, Hiroshi.

Comprehensive Chirality. 巻 5 Elsevier Ltd, 2012. p. 399-420.

研究成果: 著書/レポートタイプへの貢献

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