Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles

Such chiral phosphine-internal olefin hybrid type ligands as N-1-adamantyl-N-cinnamylaniline derivatives 1 with C(aryl)-N(amine) bond axial chirality were synthesized and utilized for the palladium-catalyzed asymmetric allylic alkylation of indoles to afford the desired products in high enantioselec...

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Published inOrganic & biomolecular chemistry Vol. 14; no. 31; pp. 7509 - 7519
Main Authors Mino, Takashi, Nishikawa, Kenji, Asano, Moeko, Shima, Yamato, Ebisawa, Toshibumi, Yoshida, Yasushi, Sakamoto, Masami
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
SUBSTITUTIONS
RESOLUTION
CHEMISTRY
ALKENE-PHOSPHINE LIGANDS
PYRROLES
1,4-ADDITION
OLEFIN LIGANDS
ALKALOIDS
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Summary:Such chiral phosphine-internal olefin hybrid type ligands as N-1-adamantyl-N-cinnamylaniline derivatives 1 with C(aryl)-N(amine) bond axial chirality were synthesized and utilized for the palladium-catalyzed asymmetric allylic alkylation of indoles to afford the desired products in high enantioselectivities (up to 98% ee).
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01354f