Practical Stereoselective Synthesis of C3‐Spirooxindole‐ and C2‐Spiropseudoindoxyl‐Pyrrolidines  via  Organocatalyzed Pictet‐Spengler Reaction/Oxidative Rearrangement Sequence | Zendy

Kondo Masaru | Zendy; Matsuyama Naoki | Zendy; Aye Tin Z. | Zendy; Mattan Irshad | Zendy; Sato Tomoyuki | Zendy; Makita Yoshinori | Zendy; Ishibashi Masami | Zendy; Arai Midori A. | Zendy; Takizawa Shinobu | Zendy; Sasai Hiroaki | Zendy

Premium

Practical Stereoselective Synthesis of C3‐Spirooxindole‐ and C2‐Spiropseudoindoxyl‐Pyrrolidines via Organocatalyzed Pictet‐Spengler Reaction/Oxidative Rearrangement Sequence

Author(s) -

Kondo Masaru,

Matsuyama Naoki,

Aye Tin Z.,

Mattan Irshad,

Sato Tomoyuki,

Makita Yoshinori,

Ishibashi Masami,

Arai Midori A.,

Takizawa Shinobu,

Sasai Hiroaki

Publication year - 2021

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.202001472

Subject(s) - chemistry , tryptamines , stereoselectivity , enantioselective synthesis , pictet–spengler reaction , combinatorial chemistry , organocatalysis , organic chemistry , stereochemistry , catalysis , tryptamine , biochemistry

A stereoselective synthetic route to chiral C3‐spirooxindole‐ and C2‐spiropseudoindoxyl‐pyrrolidines was accomplished by an enantioselective organocatalyzed Pictet‐Spengler reaction of tryptamines and isotryptamines followed by a diastereoselective oxidative rearrangement using eco‐friendly oxidants (i. e., NaOCl ⋅ 5H 2 O and Oxone®). This sequential reaction enables rapid access to chiral C3‐spirooxindole‐ and C2‐spiropseudoindoxyl‐pyrrolidines in a one‐pot process. A Wnt signaling inhibitory assay of the prepared enantioenriched spiro compounds demonstrated that they exhibited moderate activities.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research