Chiral auxiliary approach to the asymmetric Pictet-Spengler reaction of tryptamines

Authors
Kawate, T Yamanaka, M Nakagawa, M
Citation
T. Kawate et al., Chiral auxiliary approach to the asymmetric Pictet-Spengler reaction of tryptamines, HETEROCYCLE, 50(2), 1999, pp. 1033-1039
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
2
Year of publication
1999
Pages
1033 - 1039
Database
ISI
SICI code
0385-5414(19990401)50:2<1033:CAATTA>2.0.ZU;2-K
Abstract
The diastereoselective Pictet-Spengler reaction of chiral tryptamines beari ng an alpha-naphthylethyl auxiliary group was investigated. In the presence of trifluoroacetic acid as a catalyst, the Pictet-Spengler reaction of var ious aldehydes gave the corresponding tetrahydro-beta-carbolines at a diast ereoselectivity of up to 93.7.