Stereoselective Synthesis of Spiro[tetrahydropyran-3,3′-oxindole] Derivatives Employing Prins Cascade Strategy

Stereoselective Synthesis of Spiro[tetrahydropyran-3,3′-oxindole] Derivatives Employing Prins Cascade Strategy

A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct th...

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Veröffentlicht in:Organic letters 2014-12, Vol.16 (24), p.6267-6269
Hauptverfasser: Subba Reddy, B. V., Swathi, V., Swain, Manisha, Bhadra, Manika Pal, Sridhar, B., Satyanarayana, D., Jagadeesh, B.
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Boranes - chemistry
Catalysis
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Phenylbutyrates - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung:A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct the spirocycles in a one-pot operation through a Prins cascade process.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503089m