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OH-Metal hydrogen bond in Pd- and Ir-catalyzed allylic alkylations
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.ORCID-id: 0000-0002-1743-7650
2006 (engelsk)Inngår i: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, s. ORGN-259-Konferansepaper, Publicerat paper (Annet vitenskapelig)
Abstract [en]

Phosphinooxazolines carrying 4-hydroxybenzyl and 4-methoxybenzyl substituents exhibit contrasting behavior in Pd- and Ir-catalyzed allylic alkylations.  Whereas catalysts with the methoxy-contg. ligand generally provide products with high ee's, use of catalysts prepd. from the hydroxy contg. ligand results in products with low ee's or even racemates.  DFT calcns. suggest the presence of a hydrogen bond with Pd(0) as proton acceptor in the hydroxy contg. olefin Pd(0) complexes, which induces a conformational change in the ligand leading to different stereoselectivity.  We have previously obsd. the same kind of dramatic changes of enantioselectivities in palladium-catalyzed allylations upon methylation of hydroxy-contg. pyridinooxazolines and bisoxazolines.

sted, utgiver, år, opplag, sider
2006. s. ORGN-259-
Serie
Abstracts of papers of the american chemical society, ISSN 0065-7727
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-71036ISI: 000207781608341OAI: oai:DiVA.org:kth-71036DiVA, id: diva2:486428
Konferanse
232nd ACS National Meeting, San Francisco, CA
Merknad

QC 20120222

Tilgjengelig fra: 2012-01-30 Laget: 2012-01-30 Sist oppdatert: 2016-12-21bibliografisk kontrollert

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