Journal
TETRAHEDRON LETTERS
Volume 67, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.152863
Keywords
Chiral phosphines; Allylic derivatives; Cyclopentenes; [4+1] annulation; Asymmetric catalysis
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Funding
- National Natural Science Foundation of China [21472096, J1103306]
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This study reports a chiral phosphine-catalyzed asymmetric annulation reaction, which efficiently synthesizes enantio-enriched polysubstituted cyclopentenes with high stereoselectivity.
A chiral phosphine-catalyzed asymmetric [4 + 1] annulation reaction of polar 1,3-dienes and allylic derivatives is reported. Under the catalysis of P-chiral bicyclic phosphine (15 mol%), a series of 1,1-dicyano-2,4-diaryl-1,3-dienes (21 examples) readily undergo stereoselective [4 + 1] annulation reactions with allylic acetate under mild conditions, delivering enantio-enriched polysubstituted cyclopentenes in 49-89% yields and 51-98% ee. A plausible mechanism for the reaction is also discussed. (C) 2021 Elsevier Ltd. All rights reserved.
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