Asymmetric Synthesis of Allenyl Oxindoles and Spirooxindoles by a Catalytic Enantioselective Saucy–Marbet Claisen Rearrangement†
Trung Cao
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorJoshua Deitch
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorDr. Elizabeth C. Linton
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorCorresponding Author
Prof. Marisa C. Kozlowski
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)Search for more papers by this authorTrung Cao
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorJoshua Deitch
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorDr. Elizabeth C. Linton
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Search for more papers by this authorCorresponding Author
Prof. Marisa C. Kozlowski
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)
Department of Chemistry, Penn Merck High Throughput Experimentation Laboratory, University of Pennsylvania, Philadelphia, PA 19104-6323 (USA)Search for more papers by this authorFinancial support was provided by the NSF (CHE-0911713) and NIH (RO1GM087605). Partial instrumentation support was provided by the NIH for MS (1S10RR023444) and NMR (1S10RR022442) and by the NSF for an X-ray diffractometer (CHE-0840438). The invaluable assistance of Dr. Patrick Carroll in obtaining the crystal structures is gratefully acknowledged.
Graphical Abstract
Palladium(II)-Katalysatoren mit (R)-Binap oder tBuphox als Liganden L* vermitteln die erste erfolgreiche katalytische enantioselektive Saucy-Marbet-Claisen-Umlagerung. Dabei entstanden Allenyloxindole oder Spirolactone mit quartärem Zentrum mit bis zu 98 % ee.
Supporting Information
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