Fiesers' reagents for organic synthesis Volume 26 by Tse-Lok Ho

By Tse-Lok Ho

The hugely profitable Fieser & Fieser sequence has supplied a number of generations chemists and scholars with an up to date survey of the reagent literature. Reagents are indexed in alphabetical order by way of universal identify, and the short access tells how one can make it or purchase it, what it's reliable for, and the place to discover whole info. quantity 26 covers chemical literature from the center of 2008 to the tip of 2009.

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The title reagent, in either chiral series, is obtained from BINOL on consecutive treatment with BuLi and t‐BuSOCl. M. T 68, 7129 (2012) 1 1,1′‐Binaphthalene‐2,2′‐diyl N‐sulfonylaminophosphates Ring enlargement. 1 Ar R O P O O O NHSO2R (1A) Cu(OTf)2 O PhMe 10° R R R Ar (1A) Ar = 9-anthryl, R = Tol (1B) Ar = 9-phenanthryl, R = CF3 (1C) Ar = 1-pyrenyl, R = CF3 Nazarov cyclization. 3 O O R R′ Br+ O O R (1B) Br R′ 30 1,1′‐Binaphthalene‐2,2′‐diyl N‐alkylaminophosphites Cycloaddition. 4 R′ O R″ O + O R Si OH R (1C) PhF 25° H O R′ H R″ R Si O R Oxidation.

Ishihara, K. , Chakraborty, D. TL 53, 5652 (2012) 14 15 1,1′‐Binaphthalene‐2,2′‐disulfonic acid and imides R O SO3H SO3H S O S O NH O R (1) O S O S O (2A) R = 3,5-(CF3)2 (2B) R = 3,5-[(CF3)2CF] (2C) R = 3,5-(O2N)2-4-Me N O H NH (3) Addition. 4 1,1′‐Binaphthalene‐2,2′‐diyl N‐sulfonylaminophosphates 29 Cycloaddition. The pyranone synthesis pioneered by Danishefsky has many a­ pplications and numerous catalysts for inducing enantioselectivity are on record. , List, B. , Ishihara, K. M. , Du, D. , List, B.

List, B. ASC 354, 2363 (2012) 34 35 1,1′‐Binaphthalene‐2,2′‐diyl phosphites Hydrogenation. , Gennari, C. , Gennari, C. , Vidal‐Ferran, A. CEJ 17, 13978 (2011) 1 2 OR 1,1′‐Binaphthalen‐2‐ol‐2′‐phosphines and derivatives 45 1,1′‐Binaphthalen‐2‐ol‐2′‐phosphines and derivatives Substitution. 2 Different Pd species are used in the two reactions, as the t‐Boc groups in ­substrate of second reaction is acid‐sensitive. 3 Addition. 6 H N Ar R Ar (cod)2RhBF4 ent-(2B) R′ N R R′ R O NTs + COOR R O ent-(2C) CHCl3 10° NTs COOR 46 1,1′‐Binaphthalen‐2‐ol‐2′‐phosphines and derivatives Annulation.

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