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Catalytic Asymmetric Construction of Spirocycles Containing Pyrrolidine Motifs and Spiro Quaternary Stereogenic Centers via 1,3-Dipolar Cycloaddition of Azomethine Ylides with 2-Alkylidene-Cycloketones

✍ Scribed by Tang-Lin Liu; Zhao-Lin He; Qing-Hua Li; Hai-Yan Tao; Chun-Jiang Wang

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
595 KB
Volume
353
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

The first catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides with various sterically hindered α,α,β‐trisubstituted 2‐alkylidene‐cycloketones has been developed successfully with silver acetate/TF‐BiphamPhos complex for the construction of spiro heterocyclic compounds containing pyrrolidine motifs and a spiro quaternary stereogenic carbon center. The highly efficient catalytic system exhibited high reactivity, excellent diastereoselectivity, good enantioselectivity and broad substrate scope under mild conditions. Subsequent transformations led to the expedient preparation of synthetically useful spiro[pyrrolidine‐tetrahydropyranone] and spiro[pyrrolidine‐isochroman‐1‐one] without loss of the diastereo‐ and enantiomeric excesses.

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ChemInform Abstract: Morita—Baylis—Hillm
ChemInform Abstract: Morita—Baylis—Hillman Adducts as Effective Dipolarophiles in Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition with Azomethine Ylides: Asymmetric Construction of Pyrrolidine Derivatives Containing Quaternary Stereogenic Center.
✍ Huai-Long Teng; He Huang; Hai-Yan Tao; Chun-Jiang Wang 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

## Abstract The first catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides (II) with Morita—Baylis—Hillman adducts bearing an allylic hydroxyl group is described.