Conjugate-base-stabilized Brønsted acids: catalytic enantioselective Pictet-Spengler reactions with unmodified tryptamine.
A conjugate-base-stabilized Brønsted acid facilitates catalytic enantioselective Pictet-Spengler reactions with unmodified tryptamine. The chiral carboxylic acid catalyst is readily assembled in just two steps and enables the formation of β-carbolines with up to 92% ee. Achiral acid additives or in situ Boc-protection facilitate catalyst turnover.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Nisha
N
Mittal
Diana X
DX
Sun
Daniel
D
Seidel
D002243:Carbolines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
D002243:Carbolines; D002264:Carboxylic Acids; D014363:Tryptamines; C030820:tryptamine