Antibody-catalyzed asymmetric intramolecular Michael addition of aldehydes and ketones to yield the disfavored cis-product.
The development of new catalytic asymmetric reactions continues to be a major goal in organic chemistry. Here we report a novel antibody-catalyzed intramolecular Michael addition of aldehydes and ketones to enones. The reaction is enantioselective and diastereoselective with a high ee value and cis/trans ratio. This is the first example of asymmetric intramolecular Michael addition of ketones. Antibody 38C2 is the only catalyst to date capable of generating this selectivity in Michael addition products.
Weinstain
Roy
R
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel Aviv 69978, Israel.
Lerner
Richard A
RA
Barbas
Carlos F
CF
Shabat
Doron
D
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000906:Antibodies / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000906:Antibodies; D007659:Ketones