Abstract
We have developed a regiospecific and highly stereoselective strategy for constructing the five-/six-membered monocyclic and bicyclic nitrogen heterocycle skeletons using PhSe group transfer radical cyclization of alpha-phenylseleno amido esters promoted by a Lewis acid (e.g., Yb(OTf)(3)) under UV irradiation. We obtained 5-/6-exo-trig mode cyclization products for the N-allyl/homoallyl substrates, whereas the enamide substrate gave 5-endo-trig ring closure.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Free Radicals / chemical synthesis
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Free Radicals / chemistry
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Lactams / chemical synthesis*
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Lactams / chemistry
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Mesylates / chemistry*
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Molecular Structure
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Organometallic Compounds / chemistry*
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Organoselenium Compounds / chemistry*
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Stereoisomerism
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Ultraviolet Rays
Substances
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Free Radicals
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Lactams
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Mesylates
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Organometallic Compounds
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Organoselenium Compounds
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ytterbium(III) triflate