Asymmetric hydrogenation via architectural and functional molecular engineering*
نویسندگان
چکیده
RuCl2(phosphine)2(1,2-diamine) complexes, coupled with an alkaline base in 2-propanol, allows for preferential hydrogenation of a C=O function over coexisting conjugated or nonconjugated C=C linkages, a nitro group, halogen atoms, and various heterocycles. The functional group selectivity is based on the novel metal–ligand bifunctional mechanism. The use of appropriate chiral diphosphines and diamines results in rapid and productive asymmetric hydrogenation of a range of aromatic, hetero-aromatic, and olefinic ketones. The versatility of this method is manifested by the asymmetric synthesis of various biologically significant chiral compounds.
منابع مشابه
Architectural and functional engineering of chiral molecular catalysts Asymmetric Catalysis Special Feature Part I: Toward efficient asymmetric hydrogenation:
www.pnas.org/cgi/content/full/101/15/5356#otherarticles This article has been cited by other articles: E-mail Alerts . click here at the top right corner of the article or Receive free email alerts when new articles cite this article sign up in the box Subspecialty Collections www.pnas.org/cgi/collection/asymm_catalysis Asymmetric Catalysis Special Feature collection(s): This article, along wit...
متن کاملToward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts.
Asymmetric hydrogenation uses inexpensive, clean hydrogen gas and a very small amount of a chiral molecular catalyst, providing the most powerful way to produce a wide array of enantio-enriched compounds in a large quantity without forming any waste. The recent revolutionary advances in this field have entirely changed the synthetic approach to producing performance chemicals that require a hig...
متن کاملPd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers.
An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydrogenation pathway includes Brønsted acid promoted tautomerization of pyrazol-5-ols and Pd-catalyz...
متن کاملIridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents
Chiral iridium catalysts have now been used in the asymmetric hydrogenation of largely unfunctionalized olefins for a decade. Recently, they have also been applied to substrates with more exotic functional groups, including non-coordinating ones. These, unlike coordinating substituents, cannot direct asymmetric hydrogenation by rhodiumor ruthenium-based catalysts. This review discusses several ...
متن کاملAsymmetric Hydrogenation and Transfer Hydrogenation of Ketones
Optically active alcohols are important building blocks in the synthesis of fine chemicals, pharmaceuticals, agrochemicals, flavors and fragrances as well as functional materials (Arai & Ohkuma, 2011; Klingler, 2007). Furthermore, molecular hydrogen is without doubt the cleanest reducing agent, with complete atom efficiency. Therefore, the catalytic, asymmetric hydrogenation (AH) of prochiral k...
متن کامل