Organic Reactions, Volume 72 by Scott E. Denmark

By Scott E. Denmark

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 extensive applicability. The authors have had adventure with the strategies surveyed. the topics are awarded from the preparative point of view and specific awareness is given to obstacles, interfering impacts, results of constitution and the choice of experimental thoughts. each one bankruptcy comprises numerous specified approaches illustrating the numerous alterations of the strategy. every one bankruptcy includes pills that come with all of the examples of the response into account that the writer has been capable of finding.

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The scope of this reaction does not seem to have been determined. 467 No reports on aminations of sulfoxide-stabilized carbanions were found. O2 S Me O2 S 1. n-BuLi, THF, hexane, 0°, 30 min 2. 5 h (Eq. 145) H N S O2 Bn 1. n-BuLi, THF, pentane, –78°, 55 min OR 2. 2,4,6-Me3C6H2SO2N3, –78°, 6 h H H Bn + N3 Bn OR N N3 S O2 (40%) R = TBDPS N S O2 OR (24%) (Eq. 146) SO2 EtO2CN=NCO2Et, MeCN reflux, 3 h NHBu-n SO2 EtO2CNH N EtO2C (65%) (Eq. 147) NHBu-n 74 Amination of Phosphorus-Stabilized Carbanions Only one report on the amination of a phosphine oxide anion (Eq.

Reaction of α-branched aldehydes with chloramine-T in the presence of L-proline gives the racemic α-tosylamino aldehydes in high yield (Eq. 78 A similar reaction with sulfonyl azides also produces α-tosylamino aldehydes, but with modest yields and enantioselectivities (Eq. 386a CHO 1. 5 eq), CH2Cl2, 0°; rt, 1 h 2. 5 d 3. H2O CHO N NHCO2Et CO2Et (54%) 86% ee (Eq. 5 eq) SBn CHO BzOH, toluene, –15°, 16 h Ar = 3,5-(CF3)2C6H3 SBn SBn CHO EtO2CN=NCO2Et N HN CO2Et CO2Et –15°, 16 h 1. NaBH4, MeOH, 0°, 10 min 2.

TsN3, THF, 0° 2. RaNi, NaOH Bn NH2 (Eq. 66) 2. NaAlH2(OCH2CH2OMe)2, toluene, –70° to 0°, 1 h 2. Na4P2O7, H2O MgBr NH2 2. H2O 3. HCl (67%) N3 (49%) Bn NH3+ Cl– (71%) (Eq. 67) Bn The situation is more favorable when the aryl carbanion can be prepared directly from the arene by ortho lithiation. Examples are shown in Eqs. 311 Phenylthiomethyl azide (32) does not react with aryllithium reagents but this failure can be remedied by converting them into magnesium reagents (Eq. 274,275,375 Trimethylsilylmethyl azide (Eq.

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