Rhodium‐Catalyzed Asymmetric [5+2] Cycloaddition of Alkyne–Vinylcyclopropanes

Easy to scale: A rhodium‐catalyzed asymmetric intramolecular [5+2] cycloaddition of alkyne–vinylcyclopropanes has been developed. High enantioselectivities of up to >99.5 % ee have been achieved by the use of a chiral phosphoramidite ligand. The reaction can be easily scaled up and the stereochem...

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Bibliographic Details
Published in:Chemistry : a European journal 2009-09, Vol.15 (35), p.8692-8694
Main Authors: Shintani, Ryo, Nakatsu, Hiroki, Takatsu, Keishi, Hayashi, Tamio
Format: Article
Language:English
Subjects:
asymmetric catalysis
cycloaddition
phosphoramidite
rhodium
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Summary:Easy to scale: A rhodium‐catalyzed asymmetric intramolecular [5+2] cycloaddition of alkyne–vinylcyclopropanes has been developed. High enantioselectivities of up to >99.5 % ee have been achieved by the use of a chiral phosphoramidite ligand. The reaction can be easily scaled up and the stereochemical model of the present catalysis has also been proposed.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200901463