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Total Synthesis of Indolizidine Alkaloid (−)‐209D: Overriding Substrate Bias in the Asymmetric Rhodium‐Catalyzed [2+2+2] Cycloaddition
Authors:Robert T Yu  Ernest E Lee Dr  Guillaume Malik  Tomislav Rovis Prof
Institution:Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA), Fax: (+1)?970‐491‐1801
Abstract:CO! You had me at hello : The use of chiral biphenyl‐based phosphoramidite ligands on rhodium provides an efficient 2+2+2] cycloaddition between terminal alkyl alkynes and alkenyl isocyanates (see scheme). The cycloaddition proceeds through a CO migration pathway, and facilitates a rapid four‐step asymmetric synthesis of indolizidine (?)‐209D.
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Keywords:alkaloids  cycloaddition  heterocycles  isocyanates  rhodium
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