Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Carbonyl Ylides Generated from Diazoimide Derivatives and Their Synthetic Applications to Indolizidine Alkaloids

Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Carbonyl Ylides Generated from Diazoimide Derivatives and Their Synthetic Applications to Indolizidine Alkaloids

Highly enantioselective 1,3-dipolar cycloaddition reactions, catalyzed by chiral Lewis acids, between several 3-(2-alkenoyl)-2-oxazolidinones and carbonyl ylides that were generated from N-diazoacetyl lactams are described. Reactions of N-diazoacetyl lactams that possess 5-, 6-, and 7-membered rings...

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Veröffentlicht in:Journal of organic chemistry 2013-11, Vol.78 (21), p.10840-10852
Hauptverfasser: Suga, Hiroyuki, Hashimoto, Yuta, Yasumura, Shingo, Takezawa, Ryota, Itoh, Kennosuke, Kakehi, Akikazu
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container_end_page 10852
container_issue 21
container_start_page 10840
container_title Journal of organic chemistry
container_volume 78
creator Suga, Hiroyuki
Hashimoto, Yuta
Yasumura, Shingo
Takezawa, Ryota
Itoh, Kennosuke
Kakehi, Akikazu
description Highly enantioselective 1,3-dipolar cycloaddition reactions, catalyzed by chiral Lewis acids, between several 3-(2-alkenoyl)-2-oxazolidinones and carbonyl ylides that were generated from N-diazoacetyl lactams are described. Reactions of N-diazoacetyl lactams that possess 5-, 6-, and 7-membered rings were transformed to the corresponding epoxy-bridged indolizidines, quinolizidines, and 1-azabicyclo[5.4.0]undecanes with good to high enantioselectivities. Regio- and stereoselective ring-opening of the epoxy-bridged indolizidine cycloadduct gave the corresponding alcohol as a single diastereomer. The sequence of asymmetric cycloaddition followed by ring-opening was applied to the syntheses of several chiral indolizidine derivatives, including (+)-tashiromine.
doi_str_mv 10.1021/jo401837d
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title Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Carbonyl Ylides Generated from Diazoimide Derivatives and Their Synthetic Applications to Indolizidine Alkaloids
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