Traceless Rhodium‐Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β‐Aryl Ketones

نویسندگان

  • Anaïs Bouisseau
  • Ming Gao
  • Michael C Willis
چکیده

A one-pot three-step sequence involving Rh-catalyzed alkene hydroacylation, sulfide elimination and Rh-catalyzed aryl boronic acid conjugate addition gave products of traceless chelation-controlled hydroacylation employing alkyl aldehydes. The stereodefined β-aryl ketones were obtained in good yields with excellent control of enantioselectivity. Good variation of all three reaction components is possible.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles.

Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step ...

متن کامل

Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine.

A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl heteroaryl ketones under air to afford a broad spectrum of halo alcohols in high yields and good to excellent enantioselectivities (up to 99% e...

متن کامل

Ru-BICP-Catalyzed Asymmetric Hydrogenation of Aromatic Ketones.

The design and synthesis of effective enantioselective catalysts for hydrogenation of simple ketones remains a challenging problem.1 Recently, Noyori2 disclosed a ternary catalyst system consisting of Ru-BINAP-chiral diamine-KOH, which is highly efficient in the asymmetric hydrogenation of a variety of simple ketones lacking a secondary coordinating functional group. We have developed rhodium c...

متن کامل

Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides

Under Rh(I) catalysis, α-ketoamides undergo intermolecular hydroacylation with aliphatic aldehydes. A newly designed Josiphos ligand enables access to α-acyloxyamides with high atom-economy and enantioselectivity. On the basis of mechanistic and kinetic studies, we propose a pathway in which rhodium plays a dual role in activating the aldehyde for cross-coupling. A stereochemical model is provi...

متن کامل

Rhodium-catalyzed oxidative C2-acylation of indoles with aryl and alkyl aldehydes.

A rhodium-catalyzed oxidative C2-acylation of indoles with aryl and alkyl aldehydes via C-H bond activation is described. The reaction is highly atom-economic and provides easy access to a wide variety of 2-aroylindoles.

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:

دوره 22  شماره 

صفحات  -

تاریخ انتشار 2016