Synthesis of Spiro[piperidine‐3,3′‐oxindoles]  via  Gold(I)‐Catalyzed Dearomatization of  N ‐Propargyl‐ and  N ‐Homoallenyl‐2‐bromotryptamines | Zendy

Magné Valentin | Zendy; Blanchard Florent | Zendy; Marinetti Angela | Zendy; Voituriez Arnaud | Zendy; Guinchard Xavier | Zendy

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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

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.

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