Journal
ORGANIC LETTERS
Volume 23, Issue 8, Pages 2911-2914Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00554
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Funding
- M.D. Anderson Foundation
- University of Houston
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This study reports a diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes synthesized using Ma's method. These substrates undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization similar to thermal intramolecular Diels-Alder reactions, with diastereoselectivities ranging from 99:1 to 90:10 in most examples out of 29 presented.
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.
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