Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene–Imine [3 + 2] Annulation
نویسندگان
چکیده
منابع مشابه
Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers.
D-Threonine-L-tert-leucine-derived bifunctional phosphine, Cat. 11, catalyzed highly enantioselective [3+2] annulation of maleimides with allenes has been disclosed, allowing the synthesis of optically active functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers in good to high yields along with good to high enantioselectivities.
متن کاملDevelopment of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates.
This work details the development of ruthenium(II) catalysts for the enantioselective alkylation of chiral racemic secondary phosphines. The reactions proceed through the intermediacy of nucleophilic phosphido species, which have low barriers to pyramidal inversion; this allows for a dynamic kinetic asymmetric alkylation. The initially discovered [((R)-iPr-PHOX)(2)Ru(H)][BPh(4)] (6) catalyst wa...
متن کاملAsymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex.
Ruthenium phosphido complexes have been shown to be excellent nucleophiles, reacting via two-electron processes with a variety of electrophiles. A catalytic alkylation reaction was developed using an achiral ruthenium complex, which was then elaborated into a catalytic enantioselective synthesis of P-stereogenic phosphines. These useful and synthetically challenging phosphines can now be access...
متن کاملEnantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecul...
متن کاملEnantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines.
The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.
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ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2018
ISSN: 2155-5435,2155-5435
DOI: 10.1021/acscatal.8b01081