By S.L. Schreiber
Quantity 1 presents a close survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl performance. Emphasis has been put on these reagents that bring about hugely selective addition reactions. equipment are stated to choose, for instance, one carbonyl crew over one other within the related molecule, or so as to add preferentially a fraction to at least one (enantiotopic of diastereotopic) face of a carbonyl workforce. tactics that outcome from an preliminary addition to the C=X practical crew, for instance alkenations and rearrangements, also are coated during this quantity.
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Additional resources for Additions to C-X &pgr;-Bonds, Part 1, Volume 1
266 Chiral aldehydes can give (90) as single isomers. Isolation of some intermediates, and labelling studies which show that an aldehydic hydrogen ends up in the alkyne, indicate that the aldehyde is nucleophilically attacked by (89) to give a betaine, which rearranges to a diazomethylenephosphorane, which in turn undergoes a Wittig-type reaction with another molecule of aldehyde. 267 Most examples involve 6-oxoaldehydes giving α-hydroxycyclohexanones, although a 5-oxo- to -cyclopentanone case is also illustrated.
However, chiral phosphines and amines gave very low ees. 253 Aldehyde (RCHO) and nitrile (NC–CO2 Et) react at −45 ◦ C in DCM to give the corresponding cyanohydrin ethyl carbonate, R–*CH(CN)– O–CO2 Et. The catalyst used has four components: a chiral BINAP, (1R,2S)-(−)-N methylephedrine, cinchonine, and titanium isopropanoxide. Evidence for all four being essential is presented. 254 A fall-off in ee at high conversions has been explained by a mechanism involving competing asymmetric processes, and signiﬁcant retro-cyanation.
211 The latter reaction is implicated as a signiﬁcant source of perﬂuorinated carboxylic acids in the environment. Addition of Organozincs Most papers deal with diethylzinc. 218 The ee is highly dependent on the N -substituent, and ab initio molecular modelling has been used to interpret this ﬁnding. 219 Non-linear effects on the ee suggest that zinc aggregation occurs, and NMR evidence indicates that both ethyl groups react with both hydroxyls in the catalyst. 220 Comparison with simpler catalysts suggests that the new one exhibits cooperative effects between planar and central chiralities.
Additions to C-X &pgr;-Bonds, Part 1, Volume 1 by S.L. Schreiber