Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 16, Pages 8997-9002Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202017190
Keywords
β -H elimination; alkene isomerization; cycloketones; hydroacylation; rhodacycle
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Funding
- National Key R&D Program of China [2018YFE0126800]
- National Natural Science Foundation of China [21620102003, 21831005, 91856106, 21991112, 22071150]
- Shanghai Municipal Education Commission [201701070002E00030]
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A new transformation pattern for enantioselective intramolecular hydroacylation has been developed utilizing an alkene isomerization strategy. The conversion of 3-enals to chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities has been achieved. The stereoselection origin has been rationally explained based on a theoretically calculated catalytic cycle.
A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C-3- or C-3,C-5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.
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