Metal Catalyzed Allylic Alkylation: Its Development in the Trost Laboratories

Overview

Journal Tetrahedron

Specialty Chemistry

Date 2015 Aug 4

PMID 26236048

Citations 42

Authors

Barry M Trost

Affiliations

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References

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Trost B, Pissot-Soldermann C, Chen I, Schroeder G . An asymmetric synthesis of hamigeran B via a Pd asymmetric allylic alkylation for enantiodiscrimination. J Am Chem Soc. 2004; 126(14):4480-1. DOI: 10.1021/ja0497025. View

Trost B, Tang W . An efficient enantioselective synthesis of (-)-galanthamine. Angew Chem Int Ed Engl. 2002; 41(15):2795-7. DOI: 10.1002/1521-3773(20020802)41:15<2795::AID-ANIE2795>3.0.CO;2-2. View

Trost B, Xu J . Palladium-catalyzed asymmetric allylic alpha-alkylation of acyclic ketones. J Am Chem Soc. 2005; 127(49):17180-1. PMC: 2533158. DOI: 10.1021/ja055968f. View

Trost B, Chisholm J, Wrobleski S, Jung M . Ruthenium-catalyzed alkene-alkyne coupling: synthesis of the proposed structure of amphidinolide A. J Am Chem Soc. 2002; 124(42):12420-1. DOI: 10.1021/ja027883+. View

Trost B, Aponick A, Stanzl B . A convergent Pd-catalyzed asymmetric allylic alkylation of dl- and meso-divinylethylene carbonate: enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone. Chemistry. 2007; 13(34):9547-60. DOI: 10.1002/chem.200700832. View

Trost B, OBoyle B, Torres W, Ameriks M . Development of a flexible strategy towards FR900482 and the mitomycins. Chemistry. 2011; 17(28):7890-903. PMC: 3706290. DOI: 10.1002/chem.201003489. View

Trost B, Pissot-Soldermann C, Chen I . A short and concise asymmetric synthesis of hamigeran B. Chemistry. 2004; 11(3):951-9. DOI: 10.1002/chem.200400558. View

Trost B, Dudash Jr J, Dirat O . Application of the AAA reaction to the synthesis of the furanoside of C-2-epi-hygromycin A: a total synthesis of C-2-epi-hygromycin A. Chemistry. 2002; 8(1):259-68. DOI: 10.1002/1521-3765(20020104)8:1<259::aid-chem259>3.0.co;2-d. View

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Trost B, Tang W, Toste F . Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine. J Am Chem Soc. 2005; 127(42):14785-803. DOI: 10.1021/ja054449+. View

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Trost B, Frederiksen M . Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: synthesis of 3-allyl-3-aryl oxindoles. Angew Chem Int Ed Engl. 2004; 44(2):308-10. DOI: 10.1002/anie.200460335. View

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Trost B, Xu J, Schmidt T . Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates. J Am Chem Soc. 2009; 131(51):18343-57. PMC: 2804400. DOI: 10.1021/ja9053948. View

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Trost B, Shen H, Dong L, Surivet J, Sylvain C . Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications. J Am Chem Soc. 2004; 126(38):11966-83. DOI: 10.1021/ja048078t. View

14.

Trost B, Thiel O, Tsui H . DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E. J Am Chem Soc. 2002; 124(39):11616-7. DOI: 10.1021/ja0277834. View

15.

Trost B, Thaisrivongs D . Palladium-catalyzed regio-, diastereo-, and enantioselective benzylic allylation of 2-substituted pyridines. J Am Chem Soc. 2009; 131(34):12056-7. PMC: 3235048. DOI: 10.1021/ja904441a. View

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Trost B, Masters J, Lumb J, Fateen D . Asymmetric synthesis of chiral cycloalkenone derivatives palladium catalysis. Chem Sci. 2014; 5(4):1354-1360. PMC: 3992253. DOI: 10.1039/C3SC53250J. View

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Trost B, Osipov M, Dong G . A concise enantioselective synthesis of (-)-ranirestat. Org Lett. 2010; 12(6):1276-9. PMC: 2850125. DOI: 10.1021/ol100167w. View

18.

Trost B, Simas A, Plietker B, Jakel C, Xie J . Enantioselective palladium-catalyzed addition of 1,3-dicarbonyl compounds to an allene derivative. Chemistry. 2005; 11(23):7075-82. DOI: 10.1002/chem.200500826. View

19.

Trost B, Tang W . An enantioselective strategy to macrocyclic bisindolylmaleimides. An efficient formal synthesis of LY 333531. Org Lett. 2001; 3(21):3409-11. DOI: 10.1021/ol016666v. View

20.

Trost B, Jiang C . Atom economic asymmetric creation of quaternary carbon: regio- and enantioselective reactions of a vinylepoxide with a carbon nucleophile. J Am Chem Soc. 2001; 123(51):12907-8. DOI: 10.1021/ja012104v. View