Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine
نویسندگان
چکیده
The first enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines is described. In the presence of a dipeptide phosphine catalyst, a wide range of highly functionalized cyclopentenes bearing an all-carbon quaternary center were obtained in moderate to good yields and with good to excellent enantioselectivities.
منابع مشابه
Phosphine-catalyzed [3+2] annulation of α-substituted allenoates with ester-activated α,β-unsaturated imines: a novel variation of the Lu [3+2] cycloaddition reaction.
A phosphine-catalyzed [3+2] annulation reaction of α-substituted allenoates with ester-activated α,β-unsaturated imines is reported, which provides new and efficient access to highly functionalized cyclopentenes bearing one all-carbon quaternary center. This reaction also expands the scope of the famous Lu [3+2] cycloaddition reaction.
متن کاملCatalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.
Pin the amine on the gamma: A new method has been developed for the γ-addition of nitrogen nucleophiles to γ-substituted alkynoates or allenoates through intra- and intermolecular processes that are catalyzed by spirophosphine 1. An asymmetric version of this reaction affords enantioenriched pyrrolidines, indolines, and γ-amino-α,β-unsaturated carbonyl compounds.
متن کاملAsymmetric [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 کاملPhosphine-catalyzed domino reaction: a novel sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives.
We have successfully developed a novel and efficient phosphine-catalyzed sequential [2+3] and [3+2] annulation reaction of γ-substituent allenoates to construct bicyclic[3, 3, 0]octene derivatives. The protocol uses readily available γ-substituent allenoates as the starting materials, inexpensive PBu3 as the catalyst, and the corresponding products were obtained in good to excellent yields unde...
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.
متن کامل