135758-87-1Relevant articles and documents
The nucleophilic addition of α-metallated 1,3-dioxanes to planar chiral cationic η3-allylmolybdenum complexes. Synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-dienoic acid methyl ester, a key component of the Cryptophycins
Cooksey, John,Gunn, Andrew,Kocienski, Philip J.,Kuhl, Alexander,Uppal, Sukhjinder,Christopher, John A.,Bell, Richard
, p. 1719 - 1731 (2007/10/03)
Two adjacent stereogenic centres and a pendant alkene were constructed via nucleophilic addition of a 1,3-dioxan-4-ylcopper(I) reagent to a cationic η3-allylmolybdenum complex as part of a synthesis of (2E,5S,6R,7E)-6-methyl-8-phenylocta-2,7-di
Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.
Burgess, Kevin,Jennings, Lee D.
, p. 6129 - 6139 (2007/10/02)
Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of β-hydroxy-α-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of γ-hydroxy-α,β-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.