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Literature DB >> 25715172

Enantioselective synthesis of 1,2-dihydronaphthalene-1-carbaldehydes by addition of boronates to isochromene acetals catalyzed by tartaric acid.

Yi Luan¹, Keith S Barbato, Philip N Moquist, Tomohiro Kodama, Scott E Schaus.

Abstract

Tartaric acid is an ideal asymmetric catalyst as it is abundant, cheap, and environmentally friendly. (+)-Tartaric acid was found to catalyze a novel enantioselective [4 + 2] cycloaddition of isochromene acetals and vinylboronates. A variety of substituted isochromene acetals were tolerated, furnishing the desired dihydronaphthalenes and dihydrobenzofluorene products in good yields. High enantiomeric ratios (up to 98.5:1.5) and excellent diastereoselectivities (all >99:1) were observed employing 10 mol % of (+)-tartaric acid as the catalyst, in combination with 5 mol % of Ho(OTf)3.

Entities: Chemical Disease Species

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Year: 2015 PMID： 25715172 PMCID： PMC4666678 DOI： 10.1021/jacs.5b00757

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

30 in total

1. A hetero Diels-Alder approach to the synthesis of chromans (3,4-dihydrobenzopyrans) using oxonium ion chemistry: the oxa-Povarov reaction.

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2. Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols.

Authors: Tatsuo Ishiyama; Taka-aki Ahiko; Norio Miyaura
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3. Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors: Jason W J Kennedy; Dennis G Hall
Journal: J Am Chem Soc Date: 2002-10-02 Impact factor: 15.419

4. A facile microwave-assisted Diels-Alder reaction of vinylboronates.

Authors: Ariel M Sarotti; Pablo L Pisano; Silvina C Pellegrinet
Journal: Org Biomol Chem Date: 2010-09-07 Impact factor: 3.876

5. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

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7. Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

Authors: Magnus Rueping; Chandra M R Volla; Iuliana Atodiresei
Journal: Org Lett Date: 2012-08-22 Impact factor: 6.005

8. (E)-β-borylstyrene in the Diels-Alder reaction with 3,5-dibromo-2-pyrone for the syntheses of (±)-1-epi-pancratistatin and (±)- pancratistatin.

Authors: Hyun-Kyu Cho; Hwa-Yeon Lim; Cheon-Gyu Cho
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9. Chiral copper(II) phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones.

Authors: Kodai Saito; Yuki Kajiwara; Takahiko Akiyama
Journal: Angew Chem Int Ed Engl Date: 2013-11-13 Impact factor: 15.336

Enantioselective synthesis of 1,2-dihydronaphthalene-1-carbaldehydes by addition of boronates to isochromene acetals catalyzed by tartaric acid.

1. A hetero Diels-Alder approach to the synthesis of chromans (3,4-dihydrobenzopyrans) using oxonium ion chemistry: the oxa-Povarov reaction.

2. Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols.

3. Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

4. A facile microwave-assisted Diels-Alder reaction of vinylboronates.

5. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

6. Enzyme inhibiting lignans from Vitex negundo.

7. Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

8. (E)-β-borylstyrene in the Diels-Alder reaction with 3,5-dibromo-2-pyrone for the syntheses of (±)-1-epi-pancratistatin and (±)- pancratistatin.

9. Chiral copper(II) phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones.

10. Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.

1. Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates.

2. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

3. Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.

4. Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.