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  • Spiro-fused pyrrolidine, piperidine, and oxindole scaffolds from lactams.

Spiro-fused pyrrolidine, piperidine, and oxindole scaffolds from lactams.

Organic letters (2012-09-06)
Christoph Hirschhäuser, Jeremy S Parker, Matthew W D Perry, Mairi F Haddow, Timothy Gallagher
ABSTRACT

Expedient routes to three classes of novel spiro-fused pyrrolidine, piperidine, and indoline heterocycle scaffolds are described. These three-dimensional frameworks, which conform to the "rule of three", are suitably protected to allow for site-selective manipulation and functionalization. Different modes of substrate control were explored, which allow for good to excellent levels of diastereoselectivity and dispense with the need for additional chiral reagents or catalysts. The concepts developed were applied in short, formal syntheses of (±)-coerulescine and (±)-horsfiline.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Piperidine, biotech. grade, ≥99.5%
Sigma-Aldrich
Piperidine, ReagentPlus®, 99%
Sigma-Aldrich
Piperidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Pyrrolidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Pyrrolidine, ≥99.0%
Sigma-Aldrich
Pyrrolidine, FG
Sigma-Aldrich
Pyrrolidine, 99%
Sigma-Aldrich
Piperidine solution, suitable for peptide synthesis, 20% in DMF