Asymmetric synthesis of alpha,alpha-dibranched propargylamines by acetylide additions to N-tert-butanesulfinyl ketimines |
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| Authors: | Patterson Andrew W Ellman Jonathan A |
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| Institution: | Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA. |
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| 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. |
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