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 |
| 巻 | 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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All Science Journal Classification (ASJC) codes
- Chemistry(all)
これを引用
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 › 章
}
TY - CHAP
T1 - 5.17 Reduction
T2 - Pinacol Coupling
AU - Inanaga, J.
AU - Furuno, Hiroshi
PY - 2012/9/1
Y1 - 2012/9/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84902420305&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84902420305&partnerID=8YFLogxK
U2 - 10.1016/B978-0-08-095167-6.00519-X
DO - 10.1016/B978-0-08-095167-6.00519-X
M3 - Chapter
SN - 9780080951683
VL - 5
SP - 399
EP - 420
BT - Comprehensive Chirality
PB - Elsevier Ltd
ER -