1,3-Dipolar Cycloadditions to Bicyclic Olefins. V. The Stereo- and Regiochemistry of 1,3-Dipolar Cycloadditions to Several Unsymmetrical Bicyclic Olefins
نویسندگان
چکیده
منابع مشابه
Enantioselective 1,3-dipolar cycloadditions of diazoacetates with electron-deficient olefins.
[reaction: see text] A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to beta-substituted, alpha-substituted, and alpha,beta-disubstituted alpha,beta-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive alpha,beta-disubstituted dipolarophiles require elevated reaction temperatures, but still provide the corresponding pyraz...
متن کاملIridium–catalyzed 1,3–dipolar cycloadditions
1,3–Dipolar cycloaddition reactions (DCR) are atom–economic processes that permit the construction of heterocycles. Their enantioselective versions allow for the creation of up to four adjacent chiral centers in a concerted fashion. In particular, well–defined half–sandwich iridium (III) catalysts have been applied to the DCR between enals or methacrylonitrile with nitrones. Excellent yield and...
متن کاملIntramolecular cycloadditions of cyclobutadiene with olefins.
Intramolecular cycloadditions between cyclobutadiene and olefins can provide highly functionalized cyclobutene-containing products. The outcome of the reaction depends on the nature of the tether connecting the two reactive partners in the cycloaddition. Electronically unactivated olefins attached to cyclobutadiene through a three-atom, heteroatom-containing tether yield successfully the desire...
متن کاملApproach to regiochemistry using local softness in 1, 3-dipolar cycloadditions
The principle of hard and soft acids and bases is applied in the local sense to rationalize the regiochemistry in the cycloaddition reactions of a few typical 1,3-dipoles, in particular those with phosphorus-containing dipolarophiles. Local softnesses are calculated using density functional theory. It is observed that the regioselectivity can be explained using these new reactivity descriptors ...
متن کامل1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents.
In the present perspective the advances and real possibilities of 1,3-dipolar cycloadditions as key steps in the total synthesis of virus inhibitors are described. Azides, nitrones, and azomethine ylides are the most appropriate 1,3-dipoles for the synthesis of privileged structures with the highest biological responses against viruses.
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ژورنال
عنوان ژورنال: Bulletin of the Chemical Society of Japan
سال: 1978
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.51.1859