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Literature DB >> 10458800

Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts.

Abstract

Even moderately nucleophilic dienes react with simple aldehydes in the presence of a new Cr(III) catalyst in a hetero-Diels-Alder reaction [Eq. (1)]. Tetrahydropyranyl products with up to three stereogenic centers are generated in near-perfect diastereoselectivities and with greater than 90 % ee (99 % ee for the example shown). TBAF=tetrabutylammonium fluoride; TBS=tert-butyldimethylsilyl; TES=triethylsilyl.

Entities: Chemical

Year: 1999 PMID： 10458800 DOI： 10.1002/(sici)1521-3773(19990816)38:16<2398::aid-anie2398>3.0.co;2-e

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

34 in total

Review 1. Asymmetric catalysis in complex target synthesis.

Authors: Mark S Taylor; Eric N Jacobsen
Journal: Proc Natl Acad Sci U S A Date: 2004-03-12 Impact factor: 11.205

2. A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors: Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal: Chem Rev Date: 2007-05-27 Impact factor: 60.622

3. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

Authors: Brian J Albert; Ananthapadmanabhan Sivaramakrishnan; Tadaatsu Naka; Nancy L Czaicki; Kazunori Koide
Journal: J Am Chem Soc Date: 2007-02-06 Impact factor: 15.419

Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts.

Review 1. Asymmetric catalysis in complex target synthesis.

2. A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

3. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

Review 4. The continuing saga of the marine polyether biotoxins.

5. Enantioselective total synthesis of macrolide (+)-neopeltolide.

Review 6. Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

7. Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol.

8. (+)-Sorangicin A: evolution of a viable synthetic strategy.

9. Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

10. An asymmetric total synthesis of brevisamide.