Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

Literature DB >> 30297974

Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

Lukas Roiser¹, Katharina Zielke¹, Mario Waser¹.

Abstract

The formal (4+1)-cyclization between in situ generated achiral carbonyl-stabilized ammonium ylides and vinylogous p-quinone methides can be carried out under operationally simple conditions, leading to two different double bond regioisomers depending on the used conditions. Besides these racemic approaches, also a first proof-of-concept for enantioselective versions of these reactions has been obtained.

Entities: Chemical

Keywords: ammonium ylides; cyclization; quinone methides; regioisomers; stereoselectivity

Year: 2018 PMID： 30297974 PMCID： PMC6173290 DOI： 10.1055/s-0037-1610268

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

27 in total

1. Chalcogenides as organocatalysts.

Authors: Eoghan M McGarrigle; Eddie L Myers; Ona Illa; Michael A Shaw; Samantha L Riches; Varinder K Aggarwal
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

2. Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems.

Authors: Jia-Rong Chen; Xiao-Qiang Hu; Liang-Qiu Lu; Wen-Jing Xiao
Journal: Chem Rev Date: 2015-05-20 Impact factor: 60.622

3. Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer.

Authors: Liu Yang; Huayu Zheng; Lei Luo; Jiang Nan; Jingjing Liu; Yaoyu Wang; Xinjun Luan
Journal: J Am Chem Soc Date: 2015-04-10 Impact factor: 15.419

4. Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones.

Authors: Xiang-Zhi Zhang; Yu-Hua Deng; Kang-Ji Gan; Xu Yan; Ke-Yin Yu; Fang-Xin Wang; Chun-An Fan
Journal: Org Lett Date: 2017-03-24 Impact factor: 6.005

Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

1. Chalcogenides as organocatalysts.

2. Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems.

3. Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer.

4. Tandem Spirocyclopropanation/Rearrangement Reaction of Vinyl p-Quinone Methides with Sulfonium Salts: Synthesis of Spirocyclopentenyl p-Dienones.

5. Highly enantioselective synthesis of isoxazoline N-oxides.

6. Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.

7. Ammonium ylides for the diastereoselective synthesis of glycidic amides.

8. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

9. Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

10. Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

1. CF₃-Containing para-Quinone Methides for Organic Synthesis.

2. Electrophilic Reactivities of Vinyl p-Quinone Methides.