Download Comprehensive Organic Functional Group Transformations, by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees PDF

By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)

This quantity describes all tools for the synthesis of compounds containing acarbon atom singly bonded to a heteroatom substituent. the quantity is prepared in 3 elements facing sp3, sp2 and sp carbon associated with the heteroatoms. for every part cautious awareness has been given to varied positive factors similar to substitution styles, ring results, pressure results, neighbouring performance, stereochemistry, and so forth. that can mediate the synthesis pathway. Emphasis has additionally been given to the best and functional training of many of the practical teams. severe review ofthe systems permits the reader to choose equipment correct for his or her wishes. during this quantity the heteroatom can also be metal and as a result replicate a hugely polarised bonding association with the carbon substituent. Compounds containing unmarried bonds among carbon and heterofunctional teams represent the most important type and most ordinarily remodeled natural sensible teams.

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Additional resources for Comprehensive Organic Functional Group Transformations, Volume 2 (Synthesis: Carbon with One Heteroatom Attached by a Single Bond)

Example text

Ketoesters\ are reduced with higher levels of enantio! called Mar! diols ð60CJC1475Ł[ The acid! isomer ð78CC0318Ł as predicted by theoretical studies ð73T1146Ł[ Mes! borabicyclo! diboranes upon reaction with diborane[ These diboranes are con! verted to primary alcohols upon usual peroxidative workup "Scheme 1# ð56JA180Ł[ BR2 2 BH3 H2O2 NaOH BR2 BR2 OH Scheme 2 1[91[0[1[0 Stereo! pinene is a good example of the regio! based Functional Groups seen in such reactions^ the initial product of addition is diisopinocampheylborane "Ipc1BH#\ arising from regio!

Based Functional Groups seen in such reactions^ the initial product of addition is diisopinocampheylborane "Ipc1BH#\ arising from regio! heterocycloalkenes at −14>C to give trans! 1! metal complexes[ The observation that Wilkinson|s catalyst catalysed the addition of catecholborane to alkenes at ambient temperature was _rst made in 0874 ð74AG"E#767Ł^ this observation led workers to examine the reaction of allylic alcohols with the same borane using rhodium catalysis in the expectation that the presence of catalyst would allow a directing e}ect[ Thus the reaction of O!

Heterocycloalkenes at −14>C to give trans! 1! metal complexes[ The observation that Wilkinson|s catalyst catalysed the addition of catecholborane to alkenes at ambient temperature was _rst made in 0874 ð74AG"E#767Ł^ this observation led workers to examine the reaction of allylic alcohols with the same borane using rhodium catalysis in the expectation that the presence of catalyst would allow a directing e}ect[ Thus the reaction of O! isomer[ The authors o}er a description of the transition state of the reaction and conclude that the shape of the R group is rather more important than the size of R when assessing diastereoselectivity[ In any case\ the good to excellent diastereoselectivities seen in this reaction make the process powerful and of great utility to the synthetic chemist[ Allylic amines react with catecholborane under catalysis to provide "after oxidative workup# 0\2!

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