Spiroannulation by Alkylation and Reductive Cyclization of Nitriles

Spiroannulation by Alkylation and Reductive Cyclization of Nitriles

A new ring‐forming reaction has been developed in which nitriles act as 1,1‐dianion synthons with biselectrophiles. The cyclizations are highly diastereoselective and are capable of forming two adjacent quaternary centers with complete selectivity (see scheme; LiDBB=lithium di‐tert‐butylbiphenylide)...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-02, Vol.42 (7), p.818-820
Hauptverfasser: Rychnovsky, Scott D., Takaoka, Leo R.
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
annulation
Cyclization
diastereoselectivity
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
reduction
spiro compounds
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Beschreibung
Zusammenfassung:A new ring‐forming reaction has been developed in which nitriles act as 1,1‐dianion synthons with biselectrophiles. The cyclizations are highly diastereoselective and are capable of forming two adjacent quaternary centers with complete selectivity (see scheme; LiDBB=lithium di‐tert‐butylbiphenylide).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200390218