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Literature DB >> 14558791

Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts.

Tomotaka Okino¹, Yasutaka Hoashi, Yoshiji Takemoto.

Abstract

Michael reaction of malonates to nitroolefins with chiral bifunctional organocatalysts, bearing both a thiourea and tertiary amino group, afforded Michael adducts with high yields and enantioselectivities (up to 95%, up to 93% ee).

Entities: Chemical

Year: 2003 PMID： 14558791 DOI： 10.1021/ja036972z

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

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Cited

77 in total

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

Authors: Derong Ding; Cong-Gui Zhao; Qunsheng Guo; Hadi Arman
Journal: Tetrahedron Date: 2010-06-19 Impact factor: 2.457

2. Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.

Authors: Vijaya Bhasker Gondi; Michel Gravel; Viresh H Rawal
Journal: Org Lett Date: 2005-12-08 Impact factor: 6.005

3. Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Authors: Douglas E Fuerst; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2005-06-29 Impact factor: 15.419

4. Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.

Authors: G K Surya Prakash; Fang Wang; Timothy Stewart; Thomas Mathew; George A Olah
Journal: Proc Natl Acad Sci U S A Date: 2009-02-23 Impact factor: 11.205

5. Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors: Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal: J Am Chem Soc Date: 2008-04-04 Impact factor: 15.419

Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts.

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

2. Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.

3. Thiourea-catalyzed enantioselective cyanosilylation of ketones.

4. Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.

5. Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

6. On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

7. Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

8. Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

9. Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst.

10. Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives.