Enantioselective Synthesis of Axially Chiral Phthalides through Cationic [Rh^I(H₈‐binap)]‐Catalyzed Cross Alkyne Cyclotrimerization

Abstract

Easy access to axially chiral phthalides that bear one or two oxymethylene functionalities is provided by an enantioselective cross alkyne cyclotrimerization in the presence of the cationic complex [RhI{(S)‐H8‐binap}]+. The axial chirality is introduced during the formation of the benzene ring with high enantioselectivity.

Iridium‐Catalyzed Enantioselective [2+2+2] Cycloaddition of Diynes and Monoalkynes for the Generation of Axial Chiralities

“…[8] Quite independently, two groups reported an enantioselective [2 + 2 + 2] cycloaddition based on the same concept: Gutnov and Heller used a chiral Co catalyst under the photoirradiation conditions, [9] and Tanaka used a chiral Rh catalyst. [10] Related papers using enantioselective [2 + 2 + 2] cycloaddition of alkynes were published by the two groups. [11] This manuscript discloses the full details of the Ircatalyzed enantioselective [2 + 2 + 2] cycloaddition of Scheme 1.…”

Synthesis and solvent sorption characteristics of new types of tartaric acid, lactic acid and TADDOL derived receptor compounds

“…The diethylacetal 14c was obtained via reaction between 14b and methyl chloroformiate in the presence of n-BuLi. 25 The new lactic acid derivatives 7ae11a (Fig. 2) were prepared from the corresponding ester hydrolysis (LiOH) of 7be11b, similar to the tartaric acid derivatives.…”

Facile One-Pot Method for the Synthesis of Polysubstituted Phthalide Derivatives

“…[8][9][10][11][12] However, these approaches have some drawbacks such as high cost and tedious procedures. Recently, methods that construct the aromatic backbone from acyclic precursors have received growing interest because of their short synthetic steps.…”