Chiral alpha,beta-dialkoxy- and alpha-alkoxy-beta-aminostannanes: preparation and copper-mediated cross-coupling |
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Authors: | Mohapatra Suchismita Bandyopadhyay A Barma D K Capdevila Jorge H Falck J R |
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Affiliation: | Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9038, USA. |
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Abstract: | Addition of Zn(n-Bu(3)Sn)(2) to prochiral aldehydes affords anti-alpha,beta-dialkoxy- and anti-alpha-alkoxy-beta-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de). syn-Isomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(I)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration. [reaction: see text] |
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