Larry E Overman1, Mark D Rosen. 1. Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025.
Abstract
A catalytic intramolecular Heck reaction, followed by capture of the resulting η(3)-allylpalladium intermediate by a tethered diketopiperazine, is the central step in a concise synthetic route to (-)-spirotryprostatin B and three stereoisomers. This study demonstrates that an acyclic, chiral η(3)-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration.
A catalytic intramolecular Heck reaction, followed by capture of the resulting η(3)-allylpalladium intermediate by a tethered n class="Chemical">diketopiperazine, is the central step in a concise synthetic route to (-)-spirotryprostatin B and three stereoisomers. This study demonstrates that an acyclic, chiral η(3)-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration.
Authors: Ke Ding; Yipin Lu; Zaneta Nikolovska-Coleska; Su Qiu; Yousong Ding; Wei Gao; Jeanne Stuckey; Krzysztof Krajewski; Peter P Roller; York Tomita; Damon A Parrish; Jeffrey R Deschamps; Shaomeng Wang Journal: J Am Chem Soc Date: 2005-07-27 Impact factor: 15.419
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