Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones.
نویسندگان
چکیده
Functionalized cyclopentenones were synthesized by a Rh-catalyzed carbonylation of 3-acyloxy-1,4-enynes, derived from alkynes and α,β-unsaturated aldehydes. The reaction involved a Saucy-Marbet 1,3-acyloxy migration of propargyl esters and a [4 + 1] cycloaddition of the resulting acyloxy substituted vinylallene with CO.
منابع مشابه
Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.
We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most termina...
متن کاملAll-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C–H Functionalization and 1,4-Migration**
1,3-Enynes containing allylic hydrogens cis to the alkyne function as three-carbon components in rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations to produce spirodialins. The proposed mechanism of these reactions involves the alkenyl-to-allyl 1,4-rhodium(III) migration.
متن کاملKinetic Study, Modeling and Simulation of Homogeneous Rhodium-Catalyzed Methanol arbonylation to Acetic Acid
Thermodynamic restrictions and simultaneous effects of operational conditions on the homogeneous rhodium-catalyzed carbonylation of methanol are studied in this line of research. It is shown that the general NRTL-Virial model can be appropriated to study thermodynamics of the carbonylation. It is obtained that the reaction is kinetically and thermodynamically reasonable at temperatures abov...
متن کاملEnantioselective Rhodium‐Catalyzed Coupling of Arylboronic Acids, 1,3‐Enynes, and Imines by Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
A chiral rhodium complex catalyzes the highly enantioselective coupling of arylboronic acids, 1,3-enynes, and imines to give homoallylic sulfamates. The key step is the generation of allylrhodium(I) species by alkenyl-to-allyl 1,4-rhodium(I) migration.
متن کاملRhodium-catalyzed synthesis of esters from aryl iodides and alcohols: use of alcohols with/without the assistance of aldehydes as carbon monoxide and nucleophile sources
Since the rst report by Heck et al. on the palladium-catalyzed reaction of carbon monoxide with aryl halides and alcohols or amines, transition metal catalyzed cross-coupling reactions have been developed as a valuable method for creating carbon– carbon bonds. In particular, rhodium-catalyzed carbonylation with a variety of substrates has been studied. These reactions require the addition of C...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic letters
دوره 14 6 شماره
صفحات -
تاریخ انتشار 2012