Enantioselective Synthesis of Axially Chiral Biaryls through Rhodium-Catalyzed Complete Intermolecular Cross-Cyclotrimerization of Internal Alkynes

Enantioselective Synthesis of Axially Chiral Biaryls through Rhodium-Catalyzed Complete Intermolecular Cross-Cyclotrimerization of Internal Alkynes

We have developed a cationic rhodium(I)/H8-BINAP complex-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes with dialkyl acetylenedicarboxylates. This reaction was successfully applied to enantioselective synthesis of axially chiral biaryls utilizing internal alkynes bear...

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Veröffentlicht in:Organic letters 2005-07, Vol.7 (14), p.3119-3121
Hauptverfasser: Tanaka, Ken, Nishida, Goushi, Ogino, Masakazu, Hirano, Masao, Noguchi, Keiichi
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container_issue 14
container_start_page 3119
container_title Organic letters
container_volume 7
creator Tanaka, Ken
Nishida, Goushi
Ogino, Masakazu
Hirano, Masao
Noguchi, Keiichi
description We have developed a cationic rhodium(I)/H8-BINAP complex-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes with dialkyl acetylenedicarboxylates. This reaction was successfully applied to enantioselective synthesis of axially chiral biaryls utilizing internal alkynes bearing ortho-substituted phenyl and acetoxymethyl in each terminal position. The axial chirality is constructed at the formation of benzene rings with high enantioselectivity (up to 96% ee).
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title Enantioselective Synthesis of Axially Chiral Biaryls through Rhodium-Catalyzed Complete Intermolecular Cross-Cyclotrimerization of Internal Alkynes
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