Literature DB >> 16478146

Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and alpha-substituted acroleins: total synthesis of manzacidin A.

Taichi Kano1, Takuya Hashimoto, Keiji Maruoka.   

Abstract

A titanium BINOLate catalyzed asymmetric 1,3-dipolar cycloaddition reaction between alpha-substituted acroleins and alkyl diazoacetates has been developed. With this methodology in hand, chiral 2-pyrazolines containing a quaternary stereogenic center were obtained in high to excellent enantioselectivities (up to 95% ee). The synthetic utility of the optically enriched 2-pyrazoline thus obtained was demonstrated in the short synthesis of manzacidin A.

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Year:  2006        PMID: 16478146     DOI: 10.1021/ja056851u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

2.  Cinchona alkaloid catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to Δ2-pyrazolines.

Authors:  Nathaniel R Campbell; Bingfeng Sun; Ravi P Singh; Li Deng
Journal:  Adv Synth Catal       Date:  2011-11-01       Impact factor: 5.837

3.  Catalytic synthesis of nonracemic azaproline derivatives by cyclization of β-alkynyl hydrazines under kinetic resolution conditions.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-15       Impact factor: 15.336

4.  PREPARATION OF ISOPROPYL 2-DIAZOACETYL(PHENYL)CARBAMATE.

Authors:  Hubert Muchalski; Amanda B Doody; Timothy L Troyer; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2011-02-08

5.  Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center.

Authors:  Bo Chen; Wen-Dao Chu; Quan-Zhong Liu
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036

6.  Synthesis, characterization, and evaluation of a novel inhibitor of WNT/β-catenin signaling pathway.

Authors:  Zhao Yan; Zhongling Zhu; Jinghui Wang; Jian Sun; Yihui Chen; Guang Yang; Wenting Chen; Yuheng Deng
Journal:  Mol Cancer       Date:  2013-10-07       Impact factor: 27.401

7.  Direct catalytic asymmetric synthesis of pyrazolidine derivatives.

Authors:  Luca Deiana; Gui-Ling Zhao; Hans Leijonmarck; Junliang Sun; Christian W Lehmann; Armando Córdova
Journal:  ChemistryOpen       Date:  2012-06-21       Impact factor: 2.911

8.  Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji-Trost coupling.

Authors:  Sebastian Bretzke; Stephan Scheeff; Felicitas Vollmeyer; Friederike Eberhagen; Frank Rominger; Dirk Menche
Journal:  Beilstein J Org Chem       Date:  2016-06-02       Impact factor: 2.883

  8 in total

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