4.7 Article

Inter- and Intramolecular Cyclopropanations of Diazo Weinreb Amides Catalyzed by Ruthenium(II)-Amm-Pheox

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 10, Pages 1742-1746

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201601345

Keywords

Asymmetric synthesis; cyclopropanation; ruthenium catalyst; diazo Weinreb amide

Funding

  1. Japan Society for the Promotion of Science [26288087]
  2. Grants-in-Aid for Scientific Research [26288087] Funding Source: KAKEN

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Inter- and intramolecular cyclopropanations of a series of diazo Weinreb amides and trans-allylic diazo Weinreb amide derivatives have been achieved using chiral ruthenium(II)-Amm-Pheox catalyst to give the corresponding chiral cyclopropyl Weinreb amides in excellent yield (up to 99%) with excellent enantioselectivity (up to 99% ee). The chiral products could easily undergo useful synthetic transformations to give the corresponding aldehydes, alcohols and ketones in high yields and enantioselectivities.

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