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Remote substituent effects on regioselectivity in the Pauson–Khand reaction of 2-substituted norbornenes

✍ Scribed by Peter Mayo; William Tam

Book ID
108371273
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
204 KB
Volume
57
Category
Article
ISSN
0040-4020

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Effect of a remote substituent on regioselectivity in oxymercuration of unsymmetrically substituted norbornenes
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The effect of a remote substituent on the regioselectivity in the oxymercuration of unsymmetrical substituted norbornenes has been investigated. Moderate to high levels of regioselectivity were observed with both exo-and endo-substituents at C-2 of norbornenes.

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1-Methyl-norbornene ester 9 and 1-methyl-2,3-diazabicyclo[2.2.1]heptene ester 10 were employed in intermolecular Pauson-Khand reactions with various terminal alkynes 11af to give the dimethyl 1-methyltricyclo[5.2.1.0 5,9 ]dec-7-en-6one 2,3-dicarboxylates 12 and 13, and diethyl 2,3-diaza-1methyltricy