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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.