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Literature DB >> 19320506

Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate.

Liansuo Zu¹, Shilei Zhang, Hexin Xie, Wei Wang.

Abstract

An unprecedented highly enantioselective cascade oxa-Michael-Michael reaction has been developed. The simple and practical process, efficiently catalyzed by chiral diphenylprolinol TMS ether, affords a powerful access to highly functionalized synthetically useful chiral chromans. Moreover, notably a new activation mode involving an aminal is disclosed for the first time.

Entities: Chemical

Year: 2009 PMID： 19320506 DOI： 10.1021/ol9003433

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

11 in total

1. Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors: Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal: Proc Natl Acad Sci U S A Date: 2010-07-16 Impact factor: 11.205

2. Domino access to highly substituted chromans and isochromans from carbohydrates.

Authors: Markus Leibeling; Dennis C Koester; Martin Pawliczek; Svenia C Schild; Daniel B Werz
Journal: Nat Chem Biol Date: 2010-01-24 Impact factor: 15.040

3. Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors: Kerem E Ozboya; Tomislav Rovis
Journal: Chem Sci Date: 2011-09-01 Impact factor: 9.825

4. An organocascade kinetic resolution.

Authors: Patrick G McGarraugh; Stacey E Brenner-Moyer
Journal: Org Lett Date: 2011-11-15 Impact factor: 6.005

5. Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.

Authors: Stephen P Lathrop; Tomislav Rovis
Journal: J Am Chem Soc Date: 2009-09-30 Impact factor: 15.419

6. Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors: Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal: Chem Sci Date: 2017-01-30 Impact factor: 9.825

7. Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction.

Authors: Cheng-Ke Tang; Kai-Xiang Feng; Ai-Bao Xia; Chen Li; Ya-Yun Zheng; Zhen-Yuan Xu; Dan-Qian Xu
Journal: RSC Adv Date: 2018-01-17 Impact factor: 3.361