Abstract
Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and-manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes beating a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-β-structure.
| Original language | English |
|---|---|
| Pages (from-to) | 395-404 |
| Number of pages | 10 |
| Journal | Heterocycles |
| Volume | 54 |
| Issue number | 1 |
| Publication status | Published - Jan 1 2001 |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
Cite this
Lewis acid catalysis of second-generation metallosalen complexes : An explanation for stereochemistry of asymmetric hetero Diels-Alder reaction. / Mihara, Jun; Aikawa, Kohsuke; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu.
In: Heterocycles, Vol. 54, No. 1, 01.01.2001, p. 395-404.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Lewis acid catalysis of second-generation metallosalen complexes
T2 - An explanation for stereochemistry of asymmetric hetero Diels-Alder reaction
AU - Mihara, Jun
AU - Aikawa, Kohsuke
AU - Uchida, Tatsuya
AU - Irie, Ryo
AU - Katsuki, Tsutomu
PY - 2001/1/1
Y1 - 2001/1/1
N2 - Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and-manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes beating a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-β-structure.
AB - Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and-manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes beating a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-β-structure.
UR - http://www.scopus.com/inward/record.url?scp=0035101858&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035101858&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0035101858
VL - 54
SP - 395
EP - 404
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1
ER -