Helvetica Chimica Acta p. 954 - 974 (1987)
Update date:2022-08-04
Topics:
Seebach, Dieter
Beck, Albert K.
Imwinkelried, Rene
Roggo, Silvio
Wonnacott, Anne
A number of chiral 1,2- 1,3-and 1,4-diols were prepared and used as alkoxy ligands on Ti for enantioselective nucleophilic transfer of methyl, butyl, cyclopropyl, allyl, alkinyl, and phenyl groups to aromatic adehydes, as wellas for the enantioselective <4+2>cycloaddition of acrylate to cyclopentadiene.The 1,2-diols were pinane diol 7 and 1,2:5,6-diacetonide-protected mannitol 9 (Scheme 3) and tartrates.The 1,3-diols were obtained from the yeast-reduction products of 2-oxocyclopentane- and 2-oxocyclohexanecarboxylates and excess MeLi, BuLi, or PhLi (or the corresponding Grignard reagents; see 4-6).As 1,4-diols, we used the products 2 and 3 from tartrate acetals and methyl or phenyl Grignard reagents, the bis(benzaldehyde)acetal 8 of D-mannitol and o,o'-binaphthol (22).These diols were attached to the Ti-atom by azeotropic removal of i-PrOH from a mixture with
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