By Jie Jack Li;E. J. Corey
"This complete reference delves into the main points of brand name reactions which are vital to researchers. It offers an up to date account of forty-seven significant periods of practical crew alterations and in addition serves to interconnect them. The booklet comprises reports from major scientists of their strong point components - all equipped uniformly, making it effortless to entry information."--BOOK JACKET. content material: uneven synthesis. CBS relief ; Davis chiral oxaziridine reagents ; Midland aid ; Noyori catalytic uneven hydrogenation ; Sharpless uneven hydroxylation reactions -- relief. Eschweiler-Clark reductive alkylation of amines ; Gribble aid of diaryl ketones ; Luche relief ; Meerwein-Ponndorf-Verley relief ; Staudinger response ; Wharton response -- Oxidation. Baeyer-Villiger oxidation ; Brown hydroboration response ; Burgess dehydrating reagent ; Corey-Kim oxidation ; Dess-Martin periodinane oxidation ; Tamao-Kumada-Fleming oxidation ; Martin's sulfurane dehydrating reagent ; Oppenauer oxidation ; Prilezhaev response ; Rubottom oxidation ; Swern oxidation ; Wacker-Tsuji oxidation ; Woodward cis-dihydroxylation. Olefination. Chugaev removal ; Cope removal response ; Corey-Winter olefin synthesis ; Perkin response (cinnamic acid synthesis) ; Perkow vinyl phosphate synthesis ; Ramberg-Bäcklund olefin synthesis ; Shapiro response ; Zaitsev removing -- Amine synthesis. Fukuyama amine synthesis ; Gabriel synthesis ; Leuckart-Wallach response -- Carboxylic acid derivatives synthesis. Fischer-Speier esterification ; Mukaiyama esterification ; Ritter response ; Strecker amino acid synthesis ; Yamada coupling reagent ; Yamaguchi esterification -- Miscellaneous practical team manipulations. Balz-Schiemann response ; Buchwald-Hartwig reactions ; Haloform response ; Hunsdiecker response ; Japp-Klingemann hydrazone synthesis ; Krapcho decarboxylation ; Nef response ; Prins response ; Regitz diazo synthesis ; Sommelet response. summary: sensible team variations shape the guts of natural synthesis, with one sensible staff found in the beginning fabric remodeled right into a assorted practical team within the product. For reasons of this publication, this contains oxidations, discounts, uneven alterations, and different useful staff manipulations which are identify reactions. learn more...
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Additional resources for Name Reactions of Functional Group Transformations (Comprehensive Name Reactions)
During the preparation of enantiomerically pure (-)-blebbistatin, the enolate of the quinolone 61 was reacted with the Davis reagent 5 to afford the optically enriched 62 with 82% yield and 86% 54 ee. ’~ 1. NaHMDS 2. &Me Me0 / 63 / OMe SO20 #,Y 6 50%. 94% ee - &Me / Me0 64 / OMe A related procedure was utilized for the syntheses of Sch 42427 and ER-30346, mole antifungals, and (-)-tricycloillicinone; however, slight modifications in the experimental procedures were explored resulting in improved yield and ee.
4 mmol) of (+)-7 in 5 mL of THF was added dropwise. 5-1 h. The reaction mixture was extracted with diethyl ether (3 x 25 mL), and the combined organic extracts were washed with H20 (20 mL) and brine (20 mL) and dried 38 Name Reactions for Functional Group Transformations (MgS04). 6 rng (66%) of 80: mp 74-75 OC (lit. colorless oil); IR and NMR spectral data are consistent with reported values. Anal. 20. 22. 6 References 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22.
These detailed mechanistic studies have led to the following generalized mechanism of enolate oxation by oxaziridine reagents. In the hydroxylation of deoxybenzoin 10 to benzoin 15, the enolate anion 11 is formed by kinetic deprotonation with LDA. The enolate anion then performs a nucleophiiic attack on the oxygen of the oxaziridine 1 in a manner consistent with that proposed in transition state B. The hemiaminal 12 intermediate decomposes to form the alkoxide 14 and sulfonimine 13. 4 Synthetic Utility Readers are directed to a thorough review on the chemistry of Davis oxaziridine reagents through 1992.
Name Reactions of Functional Group Transformations (Comprehensive Name Reactions) by Jie Jack Li;E. J. Corey