Diastereoselective Rhodium Catalyzed [4 + 2] Cycloisomerization of Allenes

A diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes is reported. The asymmetric dienyl allenes are synthesized using the method reported by Ma. These substrates readily undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization analogous to therma...

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Bibliographic Details
Published in:Organic letters 2021-04, Vol.23 (8), p.2911-2914
Main Authors: Li, Jun, Gilbertson, Scott R
Format: Article
Language:English
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Summary:A diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes is reported. The asymmetric dienyl allenes are synthesized using the method reported by Ma. These substrates readily undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization analogous to thermal intramolecular Diels–Alder reactions. Overall, 29 examples are presented with tethers possessing nitrogen, oxygen, and carbon. Diastereoselectivities range from 99:1 to 90:10 in most examples.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00554