Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

Abstract

Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter-and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.

Synthesis of octagon-containing molecular nanocarbons

“…78 Their series of publications studying the [2 + 2 + 2] inter-and intramolecular cycloaddition protocol were the rst to achieve a catalytic and highly enantioselective synthesis of chiral tetraphenylenes (Scheme 19). 79,80 This elegant protocol gives access to highly functionalized tetraphenylenes 61, although the intrinsic nature of the substrates used derives in a limited offer of accessible structures.…”

Synthesis of tetraphenylene derivatives and their recent advances

“…In 2009, Shibata developed a catalytic and enantioselective method for the synthesis of chiral tetraphenylenes based on a [2 + 2 + 2] cycloaddition of triynes [60][61][62]. This approach gave the target tetraphenylene derivatives (96) in good yields (45-93%) with excellent enantioselectivities (up to 99%).…”

Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions

“…Recently, we focused on the construction of sulfur‐containing cyclic systems by cycloaddition . In addition, we achieved a highly enantioselective synthesis of saddle‐shaped tetraphenylene derivatives by consecutive inter‐ and intramolecular cycloadditions ,,. Against this background, we considered two types of reactions which could be used to construct chiral tribenzoheteropin skeletons (Scheme ).…”