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Synthesis of Spiro[piperidine‐3,3′‐oxindoles] via Gold(I)‐Catalyzed Dearomatization of N ‐Propargyl‐ and N ‐Homoallenyl‐2‐bromotryptamines
Author(s) -
Magné Valentin,
Blanchard Florent,
Marinetti Angela,
Voituriez Arnaud,
Guinchard Xavier
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600398
Subject(s) - chemistry , tryptamines , piperidine , propargyl , catalysis , hydrolysis , organic chemistry , medicinal chemistry , combinatorial chemistry , tryptamine , biochemistry
Abstract N ‐Propargyl‐ and N ‐homoallenyl‐2‐bromo‐β‐tryptamines undergo gold(I)‐catalyzed dearomatizing cyclizations to afford 2‐bromospiroindolenines that are in situ hydrolyzed to furnish spirooxindoles in a one‐pot process. Tryptophane derivatives (R 2 =CO 2 Et) led upon cyclization to chiral spirooxindoles in excellent diastereoselectivities.