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 inOrganic letters Vol. 23; no. 8; pp. 2911 - 2914
Main Authors Li, Jun, Gilbertson, Scott R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.04.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIGHLY ENANTIOSELECTIVE APPROACH
CYCLOADDITION
4C+3C
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00554