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 Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones.

Literature DB >> 17044689

Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones.

Juan Shen¹, Thanh Truc Nguyen, Yong-Peng Goh, Weiping Ye, Xiao Fu, Junye Xu, Choon-Hong Tan.

Abstract

Chiral bicyclic guanidine 1 was found to be an excellent catalyst for reactions between anthrones and various dienophiles. The catalyst can tolerate a range of substituents and substitution patterns, making several anthrone derivatives suitable for this reaction. Both Diels-Alder and Michael adducts were obtained in excellent yields, high regioselectivities, and high enantioselectivities. This is the first case of a highly enantioselective base-catalyzed anthrone Diels-Alder reaction.

Entities: Chemical

Year: 2006 PMID： 17044689 DOI： 10.1021/ja064636n

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

Keyword Cloud
Cited

11 in total

1. Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst.

Authors: Yi Wang; Hongming Li; Yong-Qiang Wang; Yan Liu; Bruce M Foxman; Li Deng
Journal: J Am Chem Soc Date: 2007-05-01 Impact factor: 15.419

2. Higher-Order Cyclopropenimine Superbases: Direct Neutral Brønsted Base Catalyzed Michael Reactions with α-Aryl Esters.

Authors: Eric D Nacsa; Tristan H Lambert
Journal: J Am Chem Soc Date: 2015-08-04 Impact factor: 15.419

Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones.

1. Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst.

2. Higher-Order Cyclopropenimine Superbases: Direct Neutral Brønsted Base Catalyzed Michael Reactions with α-Aryl Esters.

3. Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

4. Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions.

5. C2-symmetric bisamidines: chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones.

6. Acylammonium salts as dienophiles in Diels-Alder/lactonization organocascades.

7. Expanding the scope of Metal-Free enantioselective allylic substitutions: Anthrones.

8. Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Brønsted Base Catalysts.

9. A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis.

10. Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst.