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Catalytic Asymmetric Vinylogous Aldol-Type Reactions of Aldehydes with Allyl Phosphonate and Allyl Sulfone

351 Pages Posted: 23 Jan 2019 Sneak Peek Status: Under Review

See all articles by Wen-Jun Yue

Wen-Jun Yue

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Cheng-Yuan Zhang

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Liang Yin

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

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Abstract

Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand — (R)-DTBM-SEGPHOS was found to be the key to perfectly control both regio- and enantioselectivities. Transformations of the vinylogous products (including Horner-Wadsworth-Emmons olefination and Julia olefination) were successfully realized by virtue of the phosphonate and the sulfone moieties. Moreover, the present methodology was successful applied in the asymmetric synthesis of natural products.

Suggested Citation

Yue, Wen-Jun and Zhang, Cheng-Yuan and Yin, Liang, Catalytic Asymmetric Vinylogous Aldol-Type Reactions of Aldehydes with Allyl Phosphonate and Allyl Sulfone (January 19, 2019). Available at SSRN: https://ssrn.com/abstract=3318941 or http://dx.doi.org/10.2139/ssrn.3318941
This is a paper under consideration at Cell Press and has not been peer-reviewed.

Wen-Jun Yue

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Building 7, NO. 80 Zhongguancun Road
Beijing, Beijing 100190
China

Cheng-Yuan Zhang

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Building 7, NO. 80 Zhongguancun Road
Beijing, Beijing 100190
China

Liang Yin (Contact Author)

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Building 7, NO. 80 Zhongguancun Road
Beijing, Beijing 100190
China

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