- Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions
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A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.
- Walker, Johannes C. L.,Werrel, Simon,Donohoe, Timothy J.
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supporting information
p. 13114 - 13118
(2019/10/22)
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- Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand
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A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).
- Yu, Zhiyong,Eno, Meredith S.,Annis, Alexandra H.,Morken, James P.
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supporting information
p. 3264 - 3267
(2015/07/15)
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- Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions
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The marine natural product (+)-discodermolide was first isolated in 1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes a strategy for the alkylation of chiral enolates. Furthermore, this synthesis of discodermolide provides the first examples of the asymmetric 1,4-diboration of dienes and borylative diene-aldehyde couplings in complex-molecule synthesis. Borylation-based synthesis: The development of a strategy for stereocontrol in catalytic diene hydroboration enables the synthesis of a critical building block for the assembly of (+)-discodermolide. Combined with asymmetric catalytic diboration, hydroformylation, and borylative aldehyde-diene coupling reactions, (+)-discodermolide could then be prepared from simple hydrocarbon-based building blocks.
- Yu, Zhiyong,Ely, Robert J.,Morken, James P.
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supporting information
p. 9632 - 9636
(2014/10/15)
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- Catalyst-controlled diastereoselective hetero-Diels-Alder reactions
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The diastereoselective hetero-Diels-Alder reaction between Danishefsky's diene and chiral aldehydes is catalyzed by chiral chromium-Schiff base complexes. High levels of catalyst control are obtained in several cases, allowing access to all four stereoisomeric products through appropriate choice of aldehyde and catalyst enantiomers.
- Joly, Guy D.,Jacobsen, Eric N.
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p. 1795 - 1798
(2007/10/03)
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- Novel chiral lipoxygenase substrates: Design and synthesis. Part 2
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A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl,
- Yadav,Nanda
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p. 3223 - 3234
(2007/10/03)
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- Chemoenzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-propanediol Mono(p-Methoxybenzyl Ether)
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In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acyl
- Akeboshi, Tomohiro,Ohtsuka, Yoshikazu,Ishihara, Takashi,Sugai, Takeshi
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p. 624 - 637
(2007/10/03)
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