Premium
Asymmetric Synthesis of Novel Ferrocenyl Ligands with Planar and Central Chirality and Their Application to Pd‐Catalyzed Allylic Substitutions
Author(s) -
Enders Dieter,
Peters René,
Lochtman René,
Raabe Gerhard,
Runsink Jan,
Bats Jan W.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200010)2000:20<3399::aid-ejoc3399>3.0.co;2-d
Subject(s) - chemistry , allylic rearrangement , chirality (physics) , catalysis , planar chirality , palladium , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
An efficient and flexible asymmetric synthesis of planar chiral ferrocenyl ligands bearing a stereogenic centre at the β‐position to the metallocene backbone is described. A variety of donor groups can be independently introduced as electrophiles, thus allowing electronic and steric fine‐tuning of the ligands, which were investigated in Pd‐catalyzed enantioselective allylic substitutions. By employing a P , S ligand, the alkylation of the standard test system (±)‐1,3‐diphenyl‐2‐propenyl acetate using dimethyl malonate/BSA as the nucleophile proceeded in a quantitative yield with an ee of 97%, which is the best value reported so far in this reaction for a P∪S ligand.