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Inter‐ and Intramolecular Cyclopropanations of Diazo Weinreb Amides Catalyzed by Ruthenium(II)‐ Amm ‐Pheox
Author(s) -
Mandour Hamada S. A.,
Chanthamath Soda,
Shibatomi Kazutaka,
Iwasa Seiji
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601345
Subject(s) - diazo , chemistry , intramolecular force , allylic rearrangement , ruthenium , amide , catalysis , yield (engineering) , medicinal chemistry , organic chemistry , stereochemistry , materials science , metallurgy
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.