Journal
SYNTHESIS-STUTTGART
Volume 55, Issue 11, Pages 1724-1735Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1970-4452
Keywords
Pictet-Spengler reaction; asymmetric catalysis; Bronsted acid catalysis; heterocycles; ion pairing
Categories
Ask authors/readers for more resources
In the presence of a thiourea-carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet-Spengler reactions with a range of aldehydes. The reaction exhibits good compatibility with aromatic aldehydes, accepting diverse substituents at various positions on the ring. Electron-deficient tryptamines can also be used as substrates. Furthermore, the fluorenyl protecting group can be easily removed without affecting the enantioselectivity of the product.
In the presence of a thiourea-carboxylic acid catalyst, N-9-fluorenyltryptamines undergo highly enantioselective Pictet-Spengler reactions with a range of aldehydes. The reaction works particularly well with aromatic aldehydes, tolerating electronically diverse substituents in all ring positions. Electron-deficient tryptamines are viable substrates. Removal of the fluorenyl protecting group is readily accomplished without deterioration of product ee.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available