Abstract
Three-component coupling reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines efficiently provide cyclic N-sulfonylamidines containing free endocyclic N-H. The formation of two C-C bonds (contiguous stereogenic carbons), one O-Si bond, and one C-N bond, together with the cleavage of the chiral auxiliary (tert-butanesulfinyl group), occurs with excellent chemoselectivity, diastereoselectivity, and enantioselectivity in this one-pot cascade transformation.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Amidines / chemical synthesis*
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Amidines / chemistry
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Amines / chemical synthesis
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Combinatorial Chemistry Techniques
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Cyclization
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Glyoxylates / chemistry*
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Imines / chemistry*
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Molecular Structure
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Organosilicon Compounds / chemistry*
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Stereoisomerism
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Sulfones / chemical synthesis*
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Sulfones / chemistry
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Sulfoxides / chemical synthesis*
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Sulfoxides / chemistry
Substances
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Amidines
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Amines
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Glyoxylates
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Imines
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Organosilicon Compounds
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Sulfones
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Sulfoxides