- A facile lipase-catalyzed KR approach toward enantiomerically enriched homopropargyl alcohols
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Compounds possessing propargylic (prop-2-ynylic) system are very important building blocks for organic chemistry. Among them, preparation of enantiomeric homopropargyl alcohols (but-3-yn-1-ols) constitutes a key-challenge for asymmetric synthesis and thus
- Borowiecki, Pawe?,Dranka, Maciej
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supporting information
(2019/02/14)
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- Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide
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Synthetically useful α,β-unsaturated carbonyl compounds were obtained from gold-catalyzed oxidative rearrangement of homopropargylic ether under mild reaction conditions. Gold carbenoid and oxonium ylide are proposed as key intermediates.
- Xu, Mei,Ren, Tian-Tian,Li, Chuan-Ying
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p. 4902 - 4905,4
(2020/09/16)
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- Iterative synthesis of oligo-1,4-diols via catalytic anti-Markovnikov hydration of terminal alkynes
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A sequential, iterative synthesis of oligo-1,4-diol building blocks has been realized via (a) propargylation of an aldehyde with allenylzinc bromide, (b) alcohol protection and (c) ruthenium-catalyzed anti-Markovnikov hydration of the terminal alkyne to r
- Kribber, Thomas,Labonne, Aurelie,Hintermann, Lukas
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p. 2809 - 2818
(2008/03/14)
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- Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.
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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.
- Burgess, Kevin,Jennings, Lee D.
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p. 6129 - 6139
(2007/10/02)
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- On the Use of 3-Bromopropyne as a Reagent for the Introduction of the Pyruvate Moiety
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In the presence of metallic zinc 3-bromopropyne reacts with aldehydes to give homopropynylic alcohols which are converted to the corresponding bromohomopropynylic acetates by acetylation followed by reaction with N-bromosuccinimide and a catalytic quantity of silver acetate; these derivatives are then oxidized to γ-acetoxy-α-ketoesters with osmium tetroxide and tert-butyl hydroperoxide resulting in a convenient four step sequence for the introduction of the pyruvate moiety.
- Chen, Chen,Crich, David
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p. 1289 - 1290
(2007/10/02)
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