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

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 amount is prepared in 3 components facing sp3, sp2 and sp carbon associated with the heteroatoms. for every part cautious consciousness has been given to numerous positive aspects corresponding to substitution styles, ring results, pressure results, neighbouring performance, stereochemistry, and so forth. that may mediate the synthesis pathway. Emphasis has additionally been given to the handiest and useful practise of some of the useful teams. severe evaluation ofthe systems permits the reader to choose tools well suited for his or her wishes. during this quantity the heteroatom can also be steel and for that reason replicate a hugely polarised bonding association with the carbon substituent. Compounds containing unmarried bonds among carbon and heterofunctional teams represent the biggest classification and most typically remodeled natural practical teams.

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

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Dihydroxycyclohex! dihydroxycyclohexadienes "Equation "2## ð89JA8328\ 81CC123Ł[ Pseudo! monas strains will also hydroxylate nonaromatic substrates "Equation "3## ð65JOC2494\ 70HCA0047Ł[ X X OH P. putida (3) OH X = H, Br, Cl CO2H P. free extracts ð83TL3458Ł[ 2! aryl! 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!

Hydroxyenoates proceed stereo! isomers "Equation "06## ð77T380Ł[ The predominance of the arabino! triol in the product mixture depends on the substituent R1 present upon the pre! ), nmo OH TBDMS + TBDMS (16) 62% OH OH OH OH OH (9) CO2R1 OR2 OH OsO4 OH CO2R1 OR2 OH arabino CO2R1 + OR2 OH xylo (17) 36 Alcohols O O O OsO4, MeMgBr O O HO + 71% SnMe3 O HO HO (18) HO SnMe3 SnMe3 (10) The presence of a dimethylchlorostannyl group causes very high stereoselectivity in the cis! syn! syn tetrol "Equation "08## ð80TL0992Ł[ SnMe2Cl O O (11) OH OsO4, nmo Ph Ph OH Ph (19) Ph acetone OH OH Highly diastereoselective hydroxylations are reported to occur in the reaction of triene organo!

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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