Abstract
Addition of lithium acetylides prepared from 1-pentyne, phenylacetylene, and trimethylsilylacetylene to diverse N-tert-butanesulfinyl ketimines affords a range of alpha,alpha-dibranched propargyl sulfinamides in generally good yields (up to 87%) and with high diastereoselectivities (up to >99:1). Acidic cleavage of the tert-butanesulfinyl group provides the free alpha,alpha-dibranched propargylamines.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Chemistry, Organic / methods*
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Pargyline / analogs & derivatives*
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Pargyline / chemical synthesis
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Pargyline / chemistry
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Propylamines / chemical synthesis
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Propylamines / chemistry*
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Stereoisomerism
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Sulfonium Compounds / chemistry
Substances
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Propylamines
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Sulfonium Compounds
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propargylamine
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Pargyline