Premium
Palladium‐Catalyzed Allylic Alkylation of Doubly Deprotonated Carboxylic Acids
Author(s) -
Braun Manfred,
Meletis Panos,
Visse Robin
Publication year - 2011
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.201100372
Subject(s) - chemistry , deprotonation , palladium , tsuji–trost reaction , allylic rearrangement , catalysis , carbonate , enantioselective synthesis , carboxylic acid , medicinal chemistry , organic chemistry , alkylation , ion
Doubly deprotonated carboxylic acids undergo smooth palladium‐catalyzed carbon alkylations with the allylic substrates methyl allyl carbonate and ( E )‐methyl (pent‐3‐en‐2‐yl) carbonate to give γ,δ‐unsaturated carboxylic acids. A diastereoselective and enantioselective protocol leads to (2 S ,3 R )‐hexenoic acid in 87% ee .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom