Abstract
Treatment of an α,β-unsaturated ketone and an aldehyde with chromium (II) chloride and R3SiCl in DMF gives cross-pinacol-type coupling products, 1,2-diols selectively. The anti/syn ratios of the produced 1,2-diols are shown to depend on the reaction temperature: At lower temperatures, the anti adduct is produced selectively, but at higher temperatures, the anti/syn ratios gradually decrease. When a combination of manganese and a catalytic amount of lead are used instead of chromium(II), 1,6-diketone, a dimer of the α,β-unsaturated ketone, is produced selectively.
| Original language | English |
|---|---|
| Pages (from-to) | 17-23 |
| Number of pages | 7 |
| Journal | Chirality |
| Volume | 15 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2003 |
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Keywords
- 1,2-diol
- Chromium
- Manganese
- Pinacol-coupling
- Synthetic methods
ASJC Scopus subject areas
- Analytical Chemistry
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Cross-pinacol-type coupling reactions between α,β-unsaturated ketones and aldehydes with low-valent metals. / Takai, Kazuhiko; Morita, Ryotaro; Matsushita, Hiroshi; Toratsu, Chika.
In: Chirality, Vol. 15, No. 1, 2003, p. 17-23.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Cross-pinacol-type coupling reactions between α,β-unsaturated ketones and aldehydes with low-valent metals
AU - Takai, Kazuhiko
AU - Morita, Ryotaro
AU - Matsushita, Hiroshi
AU - Toratsu, Chika
PY - 2003
Y1 - 2003
N2 - Treatment of an α,β-unsaturated ketone and an aldehyde with chromium (II) chloride and R3SiCl in DMF gives cross-pinacol-type coupling products, 1,2-diols selectively. The anti/syn ratios of the produced 1,2-diols are shown to depend on the reaction temperature: At lower temperatures, the anti adduct is produced selectively, but at higher temperatures, the anti/syn ratios gradually decrease. When a combination of manganese and a catalytic amount of lead are used instead of chromium(II), 1,6-diketone, a dimer of the α,β-unsaturated ketone, is produced selectively.
AB - Treatment of an α,β-unsaturated ketone and an aldehyde with chromium (II) chloride and R3SiCl in DMF gives cross-pinacol-type coupling products, 1,2-diols selectively. The anti/syn ratios of the produced 1,2-diols are shown to depend on the reaction temperature: At lower temperatures, the anti adduct is produced selectively, but at higher temperatures, the anti/syn ratios gradually decrease. When a combination of manganese and a catalytic amount of lead are used instead of chromium(II), 1,6-diketone, a dimer of the α,β-unsaturated ketone, is produced selectively.
KW - 1,2-diol
KW - Chromium
KW - Manganese
KW - Pinacol-coupling
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=0037215383&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037215383&partnerID=8YFLogxK
U2 - 10.1002/chir.10148
DO - 10.1002/chir.10148
M3 - Article
C2 - 12467037
AN - SCOPUS:0037215383
VL - 15
SP - 17
EP - 23
JO - Chirality
JF - Chirality
SN - 0899-0042
IS - 1
ER -