Catalytic asymmetric ring-opening of cyclopentadiene - heterodienophile cycloadducts with organometallic reagents

Content Provider	Semantic Scholar
Author	Pineschi, Mauro Moro, Federica Del Crotti, Paolo Macchia, Franco
Copyright Year	2006
Abstract	An unprecedented catalytic asymmetric ring-opening of easily accessible 2,3-heterosubstituted norbornenes with hard alkyl metals (R-M), is able to give a practical regio- and stereoselective access to hetero-functionalized alkyl cyclopentenes in an enantioenriched form. The copper-catalyzed desymmetrization reaction with trialkylaluminums of sterically hindered and rigid, tri- or tetracyclic Diels-Alder adducts, easily available by cycloaddition reaction of cyclopentadiene with 4-phenyl-urazole and 2,3-phthalazine-1,4-dione, proved to be particularly efficient. Interestingly, the chirality of the amine part of the BINOL-based phosphoramidite is able to impose the absolute stereochemistry of the corresponding adducts.
Starting Page	463
Ending Page	467
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1351/pac200678020463
Alternate Webpage(s)	https://www.iupac.org/publications/pac/pdf/2006/pdf/7802x0463.pdf
Alternate Webpage(s)	https://doi.org/10.1351/pac200678020463
Volume Number	78
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article