Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates

Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates

A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed...

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Veröffentlicht in:Organic letters 2009-02, Vol.11 (3), p.535-538
Hauptverfasser: Dangerfield, Emma M, Timmer, Mattie S. M, Stocker, Bridget L
Format: Artikel
Sprache:eng
Schlagworte:
Amination
Carbamates - chemical synthesis
Carbamates - chemistry
Catalysis
Molecular Structure
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
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Zusammenfassung:A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed in aqueous media.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802484y