Selective 6-endo Cyclization of the Acyl Radicals onto the Nitrogen of Imine and Oxazoline C−N Bonds

Acyl radicals generated by the addition of alkyl or vinyl radicals to carbon monoxide cyclized onto the C−N bonds of imines and oxazoline with perfect 6-endo selectivity, driven by a preference for attack at nitrogen.

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 128; no. 24; pp. 7712 - 7713
Main Authors Tojino, Mami, Otsuka, Noboru, Fukuyama, Takahide, Matsubara, Hiroshi, Ryu, Ilhyong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
LACTAMS
HETEROCYCLES
PIPERIDINES
CARBON-MONOXIDE
AZAENYNES
CARBONYLATIONS
Reaction intermediate
Endo stereoisomer
Regioselectivity
Nitrogen heterocycle
Acyl
Imine
Experimental study
Tandem reaction
Piperidone derivatives
Carbonylation
Cyclization
Organic free radical
Six membered ring
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Summary:Acyl radicals generated by the addition of alkyl or vinyl radicals to carbon monoxide cyclized onto the C−N bonds of imines and oxazoline with perfect 6-endo selectivity, driven by a preference for attack at nitrogen.
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ark:/67375/TPS-S34BW61S-H
ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja0623865