By Scott E. Denmark

ISBN-10: 0470423749

ISBN-13: 9780470423745

For all volumes: the volumes of natural Reactions are collections of chapters each one dedicated to a unmarried response or a definitive section of a response, of large applicability. The authors have had event with the approaches surveyed. the topics are offered from the preparative point of view and specific realization is given to obstacles, interfering affects, results of constitution and the choice of experimental suggestions. each one bankruptcy comprises numerous specified tactics illustrating the numerous changes of the tactic. each one bankruptcy includes drugs that come with the entire examples of the response into consideration that the writer has been capable of finding.

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66, work equally well with organolithium reagents. OMe CONEt2 1. s-BuLi, TMEDA, THF, –78°, 50 min 2. PhNHCu(CN)Li, –78°, 2 h OMe CONEt2 3. O2, –78°, 30 min (63%) (Eq. 68) NHPh O 1. n-BuLi, THF, Et2O, 0°, 2 h; rt, 22 h 2. CuI, 0°, 15 min O 3. TsON(Li)CO2Bu-t, –78°, 30 min; 0°, 2 h NHCO2Bu-t O O (45%) (Eq. 69) 32 ORGANIC REACTIONS 1. s-BuLi, TMEDA, THF, –78°, 1 h 2. TsN3 N O N O 3. NaBH4, n-Bu4N+ HSO4– (Eq. 70) NH2 (50%) O O CONEt2 1. s-BuLi, THF, hexane 2. MgBr2 3. PhSCH2N3, –78° to 0°; 0°, 1 h O 4.

430 Reactions of N -acyloxazolidinone enolates with azo esters431,432 and arenesulfonyl azides433 are rapid even at very low temperatures (−100◦ ) and the diastereochemical outcome is reliably predictable. The facile removal of the chiral auxiliary and ready conversion of the azide or hydrazino ester functionalities into amines makes these reactions a standard method for the preparation of D- and L-α-amino acids. The optimum conditions have been thoroughly worked out,318,431 although a direct comparison of the diastereodirecting efficiency of various oxazolidinones does not appear to have been made for aminations.

I-Pr)2NLi, THF, –78° to –40°, 40 min 2. 1,2-(O2N)2C6H4, THF, –78° Ph Cu(CN)ZnCl Ph 3. O2, –78°, 30 min (28%) N(Pr-i)2 (Eq. 56) (Eq. 57) (60%) OMe Ph Ph MgBr + Ph THF, rt, 2 h Ph N N H N N3 46 (55%) (Eq. 58) OMe 30 ORGANIC REACTIONS In situ generated allenyltitanium complexes of type 47 are aminated by azodicarboxylic esters and the products may be degraded to α-hydrazino acids (Eq. 360 High α-symmetric induction is achieved only when R is a methyl group; when it is n-butyl or isobutyl, the enantiomeric excess in the product decreases to 55% and 27%, respectively.

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Organic Reactions, Volume 72 by Scott E. Denmark


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