Journal
ORGANOMETALLICS
Volume 36, Issue 20, Pages 4061-4069Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.7b00704
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Funding
- MEXT of Japan [15H03805]
- JSPS of Japan [JP16H01039]
- Institute for Catalysis, Hokkaido University [13B1012]
- Grants-in-Aid for Scientific Research [16K13956, 16H01039, 15H03805, 15H03780, 16K13989] Funding Source: KAKEN
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Enantioselective desymmetrization of C-s-symmetric (eta(5)-2,5-dialkenylphogpholyl)(allyldiphenylphosphine)manganese(I) dicarbonyl complexes 1 was realized by molybdenum-catalyzed asymmetric ring closing, metathesis,(ARCM), and the corresponding bridged planar-chiral phosphacymantrene derivatives 2 were obtained in good yields with excellent enantioselectivity. The enantioselectivity of the ARCM reaction Was strongly influenced by the structures of the phospholyl-bound alkenyl groups, and the highest enantioselectivity of up to 99% ee was achieved in the reaction of 1d,e, which possess the 2-inethylpropenyl substituents at the and; of the eta(5)-phoSpholides. Single-enantiomeric planar chiral 2d, which was obtained by the recrystallization of the highly enantiomerically enriched ARCM product, can serve as a Chiral ligand for the palladium-catalyzed asymmetric allylic alkylation to show good enantioselectivity in up to 74% ee.
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