Tandem Prins Strategy for the Synthesis of Spiropyrrolidine and Spiropiperidine Derivatives | Zendy

Reddy Basi V. Subba | Zendy; Yarlagadda Suresh | Zendy; Reddy C. Ravikumar | Zendy; Reddy M. Rajashekhar | Zendy; Sridhar Balasubramanyan | Zendy; Satyanarayana Dayaka | Zendy; Jagadeesh Bharatam | Zendy

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Tandem Prins Strategy for the Synthesis of Spiropyrrolidine and Spiropiperidine Derivatives

Author(s) -

Reddy Basi V. Subba,

Yarlagadda Suresh,

Reddy C. Ravikumar,

Reddy M. Rajashekhar,

Sridhar Balasubramanyan,

Satyanarayana Dayaka,

Jagadeesh Bharatam

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201500215

Subject(s) - chemistry , tandem , prins reaction , derivative (finance) , cascade reaction , cascade , aldehyde , combinatorial chemistry , organic chemistry , stereochemistry , chromatography , catalysis , materials science , composite material , financial economics , economics

Cascade cyclization of a 3‐[(3‐methylbut‐2‐enylamino)methyl]but‐3‐en‐1‐ol derivative with aldehydes in the presence of TMSOTf at 0 °C under mild conditions provides the corresponding spiropyrrolidine scaffolds in good yields. Similar cyclization of a 3‐[(4‐methylpent‐3‐enylamino)methyl]but‐3‐en‐1‐ol derivative with aldehydes affords the correponding spiropiperidine compounds. This is a new approach for the construction of biologically relevant spirocycles in a single‐step process.

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