Concepedia

Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines

Thu Minh Thi Tong, Takahiro Soeta, Takuya Suga, Keisuke Kawamoto, Yoshihito Hayashi, Yutaka Ukaji

The Journal of Organic Chemistry · 2017 · 25 citations · 31 references

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Abstract

An enantioselective formal total synthesis of (+)-manzacidin C is described. A key feature of the synthesis is the construction of two chiral centers via the asymmetric 1,3-dipolar cycloaddition of an azomethine imine to methallyl alcohol by the use of (S,S)-DIPT as a chiral auxiliary.

References

31

Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways

Risong Na, Chengfeng Jing, Qihai Xu et al. · Journal of the American Chemical Society · 2011 · 321 citations

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Enantio‐ and Diastereoselective Construction of α,α‐Disubstituted α‐Amino Acids for the Synthesis of Biologically Active Compounds

Yasufumi Ohfune, Tetsuro Shinada · European Journal of Organic Chemistry · 2005 · 321 citations

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Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by <i>N</i>-Heterocyclic Carbenes

Audrey Chan, Karl A. Scheidt · Journal of the American Chemical Society · 2007 · 319 citations · Full text

, , +12

Catalyst-Free Conjugated Addition of Thiols to α,β-Unsaturated Carbonyl Compounds in Water

Gopal L. Khatik, Raj Kumar, Asit K. Chakraborti · Organic Letters · 2006 · 280 citations

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1,3-Dipolar cycloadditions of azomethine imines

Carmén Nájera, José M. Sansano, Miguel Yus · Organic & Biomolecular Chemistry · 2015 · 242 citations · Full text

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