Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

Synlett

Volumn , Issue 1, 2010, Pages 119-122

  Rueping, Magnus ^a   Nachtsheim, Boris J ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Amino acid; Nucleophilic substitution; Organocatalysis; Protonation; Quaternary stereocenter

Indexed keywords

BRONSTED ACID; GAMMA LACTAM DERIVATIVE; INDOLE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; NUCLEOPHILICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77949904394     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218539     Document Type: Article

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44. 2 (0.3 mL) and slowly added to the cooled indole solution within 5 min. The reaction was stirred at -65°C for 48 h, and the crude reaction mixture was purified by chromatography (hexane-EtOAc, 1:1) to yield 18 mg (54%) of 2b as a yellow oil which solidified upon standing. Selected Data
45. +.
46. +.