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Literature DB >> 15339169

Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.

Abstract

The Rh2(S-DOSP)4-catalyzed reaction of vinyldiazoacetates with dihydronaphthalenes results in a highly enantioselective (91-99.6% ee) and diastereoselective (>98% de) C-H functionalization. The apparent intermolecular C-H insertion was demonstrated to be a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.

Entities: Chemical Gene

Year: 2004 PMID： 15339169 DOI： 10.1021/ja047185k

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

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Cited

13 in total

1. Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors: Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal: J Org Chem Date: 2010-03-19 Impact factor: 4.354

2. Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

Authors: Yajing Lian; Huw M L Davies
Journal: J Am Chem Soc Date: 2011-07-18 Impact factor: 15.419

3. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

Authors: Yajing Lian; Kenneth I Hardcastle; Huw M L Davies
Journal: Angew Chem Int Ed Engl Date: 2011-08-30 Impact factor: 15.336

4. Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence.

Authors: Brendan T Parr; Zhanjie Li; Huw M L Davies
Journal: Chem Sci Date: 2011-09-02 Impact factor: 9.825

Review 5. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors: Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2014-03-03 Impact factor: 15.336

6. Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors: Laura A Brozek; Michael J Ardolino; James P Morken
Journal: J Am Chem Soc Date: 2011-10-05 Impact factor: 15.419

Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.

1. Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

2. Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

3. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

4. Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence.

Review 5. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

6. Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

7. Efficient route to 4H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids.

Review 8. Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

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

10. The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.