Computationally Guided Stereocontrol of the Combined C-H Functionalization/Cope Rearrangement

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2011 Sep 28

PMID 21948433

Citations 12

Authors

Yajing Lian

Kenneth I Hardcastle

Huw M L Davies

Affiliations

Soon will be listed here.

Citing Articles

Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives.

Marichev K, Dong K, Massey L, Deng Y, De Angelis L, Wang K Nat Commun. 2019; 10(1):5328.

PMID: 31757976 PMC: 6874555. DOI: 10.1038/s41467-019-13326-8.

Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Davies H J Org Chem. 2019; 84(20):12722-12745.

PMID: 31525891 PMC: 7232105. DOI: 10.1021/acs.joc.9b02428.

Recent advances in C(sp(3))-H bond functionalization via metal-carbene insertions.

Wang B, Qiu D, Zhang Y, Wang J Beilstein J Org Chem. 2016; 12:796-804.

PMID: 27340470 PMC: 4902055. DOI: 10.3762/bjoc.12.78.

Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Xu X, Zavalij P, Doyle M Angew Chem Int Ed Engl. 2013; 52(48):12664-8.

PMID: 24123489 PMC: 3858852. DOI: 10.1002/anie.201305539.

Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Xu X, Xu X, Zavalij P, Doyle M Chem Commun (Camb). 2013; 49(27):2762-4.

PMID: 23443271 PMC: 3829720. DOI: 10.1039/c3cc41119b.

References

Horino Y, Yamamoto T, Ueda K, Kuroda S, Toste F . Au(I)-Catalyzed cycloisomerizations terminated by sp(3) C-H bond insertion. J Am Chem Soc. 2009; 131(8):2809-11. PMC: 2880645. DOI: 10.1021/ja808780r. View

Davies H, Jin Q . Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement. J Am Chem Soc. 2004; 126(35):10862-3. DOI: 10.1021/ja047185k. View

Dai X, Wan Z, Kerr R, Davies H . Synthetic and isolation studies related to the marine natural products (+)-elisabethadione and (+)-elisabethamine. J Org Chem. 2007; 72(6):1895-900. DOI: 10.1021/jo0618167. View

Tsai A, Bergman R, Ellman J . Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation. J Am Chem Soc. 2008; 130(20):6316-7. PMC: 2713182. DOI: 10.1021/ja8012159. View

Hansen J, Gregg T, Ovalles S, Lian Y, Autschbach J, Davies H . On the mechanism and selectivity of the combined C-H activation/Cope rearrangement. J Am Chem Soc. 2011; 133(13):5076-85. DOI: 10.1021/ja111408v. View

Kang Y, Kim S, Kim D . Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines. J Am Chem Soc. 2010; 132(34):11847-9. DOI: 10.1021/ja103786c. View

Davies H, Dai X, Long M . Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin a and (-)-elisapterosin B. J Am Chem Soc. 2006; 128(7):2485-90. DOI: 10.1021/ja056877l. View

Thu H, Tong G, Huang J, Chan S, Deng Q, Che C . Highly selective metal catalysts for intermolecular carbenoid insertion into primary C-H bonds and enantioselective C-C bond formation. Angew Chem Int Ed Engl. 2008; 47(50):9747-51. DOI: 10.1002/anie.200803157. View

Davies H, Manning J . C-H activation as a strategic reaction: enantioselective synthesis of 4-substituted indoles. J Am Chem Soc. 2006; 128(4):1060-1. DOI: 10.1021/ja057768+. View

10.

Davies H, Beckwith R . Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion. Chem Rev. 2003; 103(8):2861-904. DOI: 10.1021/cr0200217. View

11.

Liang C, Collet F, Robert-Peillard F, Muller P, Dodd R, Dauban P . Toward a synthetically useful stereoselective C-H amination of hydrocarbons. J Am Chem Soc. 2007; 130(1):343-50. DOI: 10.1021/ja076519d. View

12.

Nadeau E, Ventura D, Brekan J, Davies H . Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes. J Org Chem. 2010; 75(6):1927-39. PMC: 2921541. DOI: 10.1021/jo902644f. View

13.

Li Q, Yu Z . Conjugated diene-assisted allylic C-H bond activation: cationic Rh(I)-catalyzed syntheses of polysubstituted tetrahydropyrroles, tetrahydrofurans, and cyclopentanes from ene-2-dienes. J Am Chem Soc. 2010; 132(13):4542-3. DOI: 10.1021/ja100409b. View

14.

Davies H, Stafford D, Hansen T . Catalytic asymmetric synthesis of diarylacetate and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline. Org Lett. 2000; 1(2):233-6. DOI: 10.1021/ol9905699. View

15.

Colby D, Bergman R, Ellman J . Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem Rev. 2009; 110(2):624-55. PMC: 2820156. DOI: 10.1021/cr900005n. View

16.

Shi B, Zhang Y, Lam J, Wang D, Yu J . Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids. J Am Chem Soc. 2009; 132(2):460-1. PMC: 2806936. DOI: 10.1021/ja909571z. View

17.

Lian Y, Davies H . Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles. Org Lett. 2010; 12(5):924-7. PMC: 2921947. DOI: 10.1021/ol9028385. View

18.

Schwartz B, Denton J, Lian Y, Davies H, Williams C . Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E. J Am Chem Soc. 2009; 131(23):8329-32. PMC: 2717789. DOI: 10.1021/ja9019484. View

19.

Davies H, Denton J . Application of donor/acceptor-carbenoids to the synthesis of natural products. Chem Soc Rev. 2009; 38(11):3061-71. PMC: 3397165. DOI: 10.1039/b901170f. View

20.

Chen K, Richter J, Baran P . 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization. J Am Chem Soc. 2008; 130(23):7247-9. DOI: 10.1021/ja802491q. View