Journal of the American Chemical Society p. 8186 - 8190 (1985)
Update date:2022-08-10
Topics:
Roush, William R.
Walts, Alan E.
Hoong, Lee K.
The preparation and aldehyde addition reactions of the title compounds (1a-c) are described.These tartrate ester based reagents are the most highly enetioselective group of allylboronate esters reported to date.Reagent 1b prepared from diisopropyl tartrate reacts with achiral aldehydes to give homoallylic alcohols in good yield and high enantioselectivity (71-87percent ee).Interestingly, the greatest selectivity is obtained with α-branched aldehydes such as pivaldehyde (82percent ee) and cyclohexanecarboxaldehyde (87percent ee).These reagents also exhibit useful levels of matched and mismatched diastereoselection in reactions with chiral aldehydes.For example, the reaction of glyceraldehyde acetonide (4) and 1b is selective either for erythro alcohol 6 (96:4) or the threo diastereomer 7 (92:8) depending on the chirality of 1b and the reaction solvent.The asymmetric induction in these reactions appears to originate from a novel stereoelectronic effect involving n/n repulsive interactions between the aldehydic oxygen atom and an ester carbonyl in the disfavored transition state B.
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