Catalytic enantioselective Dieckmann-type annulation: Synthesis of pyrrolidines with quaternary stereogenic centers

Jonathan D. Hargrave; Joseph C. Allen; Gabriele Kociok-Köhn; Gerwyn Bish; Christopher G. Frost

doi:10.1002/anie.200907067

Catalytic enantioselective Dieckmann-type annulation: Synthesis of pyrrolidines with quaternary stereogenic centers

Jonathan D. Hargrave, Joseph C. Allen, Gabriele Kociok-Köhn, Gerwyn Bish, Christopher G. Frost

Chemistry

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A new trick for an old dog: A Dieckmanntype cycllzation was used to synthesize the title compounds with up to 96% ee (see scheme; Bn = benzyl). The presence of a β coordinating functionality in the substrate Induces a competition between cycllzation and elimination pathways that Is influenced by the nature of the chiral llgand. A mechanistic rationale Is proposed to account for these observations.

Original language	English
Pages (from-to)	1825-1829
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	10
DOIs	https://doi.org/10.1002/anie.200907067
Publication status	Published - 1 Mar 2010

Keywords

(Figure Presented) Asymmetric catalysis
Conjugate addition
Dieckmann condensation
Domino catalysis
Rhodium

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AU - Kociok-Köhn, Gabriele

AU - Bish, Gerwyn

AU - Frost, Christopher G.

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KW - (Figure Presented) Asymmetric catalysis

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Catalytic enantioselective Dieckmann-type annulation: Synthesis of pyrrolidines with quaternary stereogenic centers

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Keywords

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