Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
| Autor: | Satoshi Ueda, Masanari Kimura, Yoshinao Tamaru, Keisuke Kojima |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Aldimine Chemistry Lactol Organic Chemistry chemistry.chemical_element General Medicine Diphenylzinc Biochemistry Medicinal chemistry Aldehyde Catalysis chemistry.chemical_compound Nickel Drug Discovery Organic chemistry Connection (algebraic framework) Alkyl Isoprene |
| Zdroj: | Tetrahedron. 62:7512-7520 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2006.03.116 |
| Popis: | Ni(acac) 2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous ( E )-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes ( 1 ) in excellent yields. Aliphatic aldehydes react similarly and give ( E )-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes ( 1 ) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed ( E )-1-arylamino-1-alkyl- 4 - methyl -5-phenyl-3-pentenes ( 1′ ) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish ( E )-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols ( 4 ) and ( E )-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols ( 5 ), respectively, in good yields with excellent E -stereoselectivity. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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