Phosphine-Catalyzed Asymmetric [3+2] Cyclization of Oxetane MBH Carbonates and Thioaurones

We have successfully applied 3-oxetanone-derived MBH carbonates in the phosphine-catalyzed asymmetric [3+2] cyclization with activated thioaurones. With l-threonine-derived amide phosphine as the catalyst, a series of oxetane bis-spiro cyclopentene skeletons, involving two spiral scaffold with vicinal tertiary and quaternary stereocenters, were constructed in good yield with good enantioselectivity and moderate to good diastereoselectivity.

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Publication Details

Journal
Synthesis
Published
2025-10-08
DOI
https://doi.org/10.1055/a-2718-6602
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Phosphine-Catalyzed Asymmetric [3+2] Cyclization of Oxetane MBH Carbonates and Thioaurones

Weijun Yao, Shuaijun Ding, Han Xiao, Zhen Wang
Synthesis
Synthesis and Catalytic Reactions
article

Phosphine-Catalyzed Asymmetric [3+2] Cyclization of Oxetane MBH Carbonates and Thioaurones

Weijun Yao, Shuaijun Ding, Han Xiao, Zhen Wang
article en

Abstract

We have successfully applied 3-oxetanone-derived MBH carbonates in the phosphine-catalyzed asymmetric [3+2] cyclization with activated thioaurones. With l-threonine-derived amide phosphine as the catalyst, a series of oxetane bis-spiro cyclopentene skeletons, involving two spiral scaffold with vicinal tertiary and quaternary stereocenters, were constructed in good yield with good enantioselectivity and moderate to good diastereoselectivity.

SynthesisVol. 57(24)
Zhejiang Sci-Tech University (CN), Chongqing University (CN), Chongqing Medical and Pharmaceutical College (CN)
Openalex Percentile: Top 79%
Synthesis and Catalytic Reactions
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