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Literature DB >> 20161684

Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles.

Abstract

2-Amino-8-oxo-tetrahydro-4H-chromene-3-carbonitriles were synthesized for the first time from a tandem Michael addition - cyclization reaction between cyclohexane-1,2-dione and benzylidenemalononitriles. An enantioselective synthesis of these compounds was achieved in moderate ee values (up to 63% ee) by using a cinchona alkaloid-derived thiouea catalyst.

Entities: Chemical Disease Species

Year: 2010 PMID： 20161684 PMCID： PMC2821098 DOI： 10.1016/j.tetlet.2009.12.139

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

25 in total

1. A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure.

Authors: Travis Dudding; Ahmed M Hafez; Andrew E Taggi; Ty R Wagerle; Thomas Lectka
Journal: Org Lett Date: 2002-02-07 Impact factor: 6.005

2. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening.

Authors: Nicolas Foloppe; Lisa M Fisher; Rob Howes; Andrew Potter; Alan G S Robertson; Allan E Surgenor
Journal: Bioorg Med Chem Date: 2006-03-29 Impact factor: 3.641

3. Control of diastereoselectivity in tandem asymmetric reactions generating nonadjacent stereocenters with bifunctional catalysis by cinchona alkaloids.

Authors: Baomin Wang; Fanghui Wu; Yi Wang; Xiaofeng Liu; Li Deng
Journal: J Am Chem Soc Date: 2007-01-31 Impact factor: 15.419

4. Cascade Michael--aldol reactions promoted by hydrogen bonding mediated catalysis.

Authors: Liansuo Zu; Jian Wang; Hao Li; Hexin Xie; Wei Jiang; Wei Wang
Journal: J Am Chem Soc Date: 2007-02-07 Impact factor: 15.419

5. Catalytic enantioselective synthesis of flavanones and chromanones.

Authors: Margaret M Biddle; Michael Lin; Karl A Scheidt
Journal: J Am Chem Soc Date: 2007-03-10 Impact factor: 15.419

6. Asymmetric organocatalytic domino Michael/aldol reactions: enantioselective synthesis of chiral cycloheptanones, tetrahydrochromenones, and polyfunctionalized bicyclo[3.2.1]octanes.

Authors: Magnus Rueping; Alexander Kuenkel; Francisco Tato; Jan W Bats
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. Control of four stereocenters in an organocatalytic domino double Michael reaction: efficient synthesis of multisubstituted cyclopentanes.

Authors: Bin Tan; Zugui Shi; Pei Juan Chua; Guofu Zhong
Journal: Org Lett Date: 2008-07-11 Impact factor: 6.005

Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles.

1. A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure.

2. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening.

3. Control of diastereoselectivity in tandem asymmetric reactions generating nonadjacent stereocenters with bifunctional catalysis by cinchona alkaloids.

4. Cascade Michael--aldol reactions promoted by hydrogen bonding mediated catalysis.

5. Catalytic enantioselective synthesis of flavanones and chromanones.

6. Asymmetric organocatalytic domino Michael/aldol reactions: enantioselective synthesis of chiral cycloheptanones, tetrahydrochromenones, and polyfunctionalized bicyclo[3.2.1]octanes.

7. Control of four stereocenters in an organocatalytic domino double Michael reaction: efficient synthesis of multisubstituted cyclopentanes.

8. Synthesis of new dihydropyrazines with DNA strand-breakage activity.

9. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents.

10. Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles.

1. Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael-Henry reaction.

2. Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates.

3. Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole.