Schuette, Jutta, Ye, Shute and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2011). Enantioselective Access to 3-Methylene-1H-indanol through Asymmetric Domino Allylstannylation-Heck Reaction. Synlett (18). S. 2725 - 2730. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

By screening various chiral P,P-ligands in the palladium-catalyzed reaction of ortho-iodobenzaldehyde with allyl tributylstannane, a suitable ligand (Taniaphos) was identified that affords 3-methylene-1-indanol with an enantioselectivity of 96% ee. This result indicates that a ligated palladium intermediate is involved in the chirogenic step of the catalytic cycle (intramolecular electrophilic activation of the aldehyde function by ortho-palladation).

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Schuette, JuttaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Ye, ShuteUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-486840
DOI: 10.1055/s-0031-1289539
Journal or Publication Title: Synlett
Number: 18
Page Range: S. 2725 - 2730
Date: 2011
Publisher: GEORG THIEME VERLAG KG
Place of Publication: STUTTGART
ISSN: 1437-2096
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PHOSPHINE-PHOSPHITE-LIGANDS; BIDENTATE CHELATE LIGANDS; CIRCULAR-DICHROISM; ALLYLATION; REAGENTS; ALDEHYDES; HYDROGENATION; HYDROBORATION; ALKYLATION; TDDFTMultiple languages
Chemistry, OrganicMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/48684

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