Structure-Based Rationale for Selectivity in the Asymmetric Allylic Alkylation of Cycloalkenyl Esters Employing the Trost ‘Standard Ligand’ (TSL): Isolation, Analysis and Alkylation of the Monomeric form of the Cationic 3-Cyclohexenyl Complex [(3-c- C6H9)Pd(TSL)]+

نویسندگان

  • Craig P. Butts
  • Emane Filali
  • Guy C. Lloyd-Jones
چکیده

Citation for published version: Butts, CP, Filali, E, Lloyd-jones, GC, Norrby, P, Sale, DA & Schramm, Y 2009, 'Structure-Based Rationale for Selectivity in the Asymmetric Allylic Alkylation of Cycloalkenyl Esters Employing the Trost ‘Standard Ligand’ (TSL): Isolation, Analysis and Alkylation of the Monomeric form of the Cationic 3-Cyclohexenyl Complex [(3-c-C6H9)Pd(TSL)]+' Journal of the American Chemical Society, vol 131, no. 29, pp. 9945–9957. DOI: 10.1021/ja8099757

برای دانلود 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

Chiral ferrocene-based phosphine-imine and sulfur-imine ligands for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters

Chiral ferrocene-based phosphine-imine ligands 1–3 and sulfur-imine ligand 4 were applied in the palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters. The results revealed that the substitutents in aryl ring, ferrocenylmethyl and benzyliene position strongly affected the enantioselective induction of phosphine-imine ligands, and the most stereoselective ligand was ferrocenyl...

متن کامل

Construction of Tertiary Chiral Centers by Pd-catalyzed Asymmetric Allylic Alkylation of Prochiral Enolate Equivalents.

The palladium-catalyzed decarboxylative allylic alkylation of enol carbonates derived from lactams and ketones is described. Employing these substrates with an electronically tuned Pd catalyst system trisubstituted chiral centers are produced. These stereocenters have been previously challenging to achieve using Pd complex/chiral P-N ligand systems.

متن کامل

Asymmetric allylic alkylation, an enabling methodology.

The diversity of mechanisms for enantiodiscrimination and of bond types that can be formed make Pd-catalyzed asymmetric allylic alkylation a powerful key step for simplification of synthetic strategy to complex molecular targets. Using a wide range of different classes of compounds including alkaloids, polyhydrofurans, nucleosides and carbanucleosides, cyclohexitols and cyclopentitols, chromane...

متن کامل

Catalytic asymmetric reactions via p-allylpalladium complexes coordinated with chiral monophosphine ligands

Chiral monophosphines (MOPs), whose chirality is due to biaryl axial chirality, are prepared from enantiometrically pure 2,2%-dihydroxy-1,1%-binaphthyl and 3,3%-dihydroxy-4,4%-biphenanthryl. The representatives are 2-(diphenylphosphino)-2%-methoxy1,1%-binaphthyl (MeO–MOP and 3-(diphenylphosphino)-3%-methoxy-4,4%-biphenanthryl (MOP–phen). The palladium complexes coordinated with the MOP ligands ...

متن کامل

Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles.

A range of primary allylic amines were resolved with selectivity factors of up to 491 through [Pd(allyl)Cl]2/(S)-BINAP-catalyzed and mesitylsulfonyl hydrazide-accelerated asymmetric allylic alkylation of malononitriles involving enantioselective C-N bond cleavage under aerobic conditions. Moreover, the reaction proved useful for the asymmetric synthesis of α-branched allyl-substituted malononit...

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

برای دانلود 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

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2017