Catalytic asymmetric synthesis using chirality-switchable helical polymer as a chiral ligand

Michinori Suginome; Takeshi Yamamoto; Yuuya Nagata; Tetsuya Yamada; Yuto Akai

doi:10.1351/PAC-CON-11-08-23

Publicly Available Published by De Gruyter February 3, 2012

Catalytic asymmetric synthesis using chirality-switchable helical polymer as a chiral ligand

Michinori Suginome , Takeshi Yamamoto , Yuuya Nagata , Tetsuya Yamada and Yuto Akai

From the journal Pure and Applied Chemistry

https://doi.org/10.1351/PAC-CON-11-08-23

Single-handed PQXphos, i.e., helical poly(quinoxaline-2,3-diyl)s bearing diarylphosphino pendant groups, served as remarkable chiral ligands in palladium-catalyzed asymmetric hydrosilylation of styrenes and asymmetric biaryl synthesis by Suzuki–Miyaura coupling, affording up to 98 % enantiomeric excess (e.e.) in both reactions. A palladium complex of high-molecular-weight variant (1000mer) of PQXphos could be reused eight times by virtue of the formation of an insoluble polymer complex. PQXphos underwent solvent-dependent inversion of the helical sense, enabling production of either of two enantiomeric products using a single PQXphos.

Keywords: asymmetric catalysis; cross-coupling reactions; helical polymer; helix inversion; hydrosilylation; macromolecular chemistry; organometallic chemistry; palladium catalysis; phosphine ligand; polymerization; switch of chirality

Conference

International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 16th, Shanghai, China, 2011-07-24–2011-07-28

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Online erschienen: 2012-2-3

Erschienen im Druck: 2012-2-3

Catalytic asymmetric synthesis using chirality-switchable helical polymer as a chiral ligand

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