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Synthesis, Properties and Applications of BICAP: a New Family of Carbazole‐Based Diphosphine Ligands
Author(s) -
Botman Peter N. M.,
Fraanje Jan,
Goubitz Kees,
Peschar René,
Verhoeven Jan W.,
van Maarseveen Jan H.,
Hiemstra Henk
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303241
Subject(s) - chemistry , phosphine , carbazole , rhodium , denticity , ruthenium , catalysis , nitrogen , combinatorial chemistry , asymmetric hydrogenation , medicinal chemistry , stereochemistry , polymer chemistry , organic chemistry , enantioselective synthesis , crystal structure
A new family of bidentate phosphine ligands based on the biscarbazole backbone has been synthesized and applied in the ruthenium‐ and rhodium‐catalyzed asymmetric hydrogenations of methyl acetoacetate and dimethyl itaconate. The nitrogen atoms in these BICAP ligands allow facile introduction of substituents providing structurally similar, but electronically different ligands, which were used to fine‐tune these reactions to 98% and 55% ee, respectively.