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Literature DB >> 12000301

Catalyst-controlled diastereoselective hetero-Diels-Alder reactions.

Abstract

[reaction: see text] The diastereoselective hetero-Diels-Alder reaction between Danishefsky's diene and chiral aldehydes is catalyzed by chiral chromium-Schiff base complexes. High levels of catalyst control are obtained in several cases, allowing access to all four stereoisomeric products through appropriate choice of aldehyde and catalyst enantiomers.

Entities: Chemical

Mesh：

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Year: 2002 PMID： 12000301 DOI： 10.1021/ol0258785

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

Authors: Paul A Wender; Brian A Loy; Adam J Schrier
Journal: Isr J Chem Date: 2011-03-24 Impact factor: 3.333

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

Authors: Amos B Smith; Shuzhi Dong; Richard J Fox; Jehrod B Brenneman; John A Vanecko; Tomohiro Maegawa
Journal: Tetrahedron Date: 2011-12-23 Impact factor: 2.457

4. An enantioselective total synthesis of (+)-peloruside A.

Authors: Meredeth A McGowan; Christian P Stevenson; Matthew A Schiffler; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2010-08-16 Impact factor: 15.336

5. An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

Authors: Amos B Smith; Shuzhi Dong
Journal: Org Lett Date: 2009-03-05 Impact factor: 6.005

Catalyst-controlled diastereoselective hetero-Diels-Alder reactions.

1. Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

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

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

4. An enantioselective total synthesis of (+)-peloruside A.

5. An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

6. Enantioselective catalytic transannular ketone-ene reactions.

7. Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates.

8. Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery.