- Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
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An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification. A highly regioselective intermolecular haloetherification that proceeds with excellent enantioselectivity, catalyzed by cinchona alkaloid dimers, is reported. The regioselectivity is preserved for unbiased alkyl substituted allyl amides with either E or Z geometry. (DHQD)2PHAL=hydroquinidine 1,4-phthalazinediyl diether.
- Soltanzadeh, Bardia,Jaganathan, Arvind,Staples, Richard J.,Borhan, Babak
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supporting information
p. 9517 - 9522
(2015/08/11)
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- Benzylguanidines and other galegine analogues inducing weight loss in mice
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Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; ± SEM) of -19.7 ± 1.0, -11.0 ± 0.7, and -7.3 ± 0.8 in BALB/c, ob/ob, and DIO models, respectively.
- Coxon, Geoffrey D.,Furman, Brian L.,Harvey, Alan L.,McTavish, John,Mooney, Mark H.,Arastoo, Mahmoud,Kennedy, Alan R.,Tettey, Justice M.,Waigh, Roger D.
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supporting information; experimental part
p. 3457 - 3463
(2010/03/25)
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- WEIGHT REDUCING COMPOUNDS
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The present invention relates to compounds which find use as weight reducing agents, and find use in treating obesity and/or excess adiposity.
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Page/Page column 15; 16
(2009/09/04)
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- Heteroatom-bearing ligands and metal complexes thereof
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Novel compounds containing a heteroatom-bearing bridge and novel complexes of these compounds with metals. The novel compounds and complexes are useful in diagnostic and therapeutic methods.
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- Synthesis of Amido-ureas and the Nature of Caracasanamide, the Hypotensive Principle of Verbesina caracasana
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Syntheses of the (E)-1 and (Z)-2 forms of 1-(3-methylbut-2-enyl)-3-(4-butyl)urea, proposed structures for the natural hypotensive caracasanamide, have been carried out.The compounds were found not to be identical wit
- Crombie, Leslie,Jarrett, Sandra R. M.
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p. 3179 - 3184
(2007/10/02)
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- PALLADIUM(0) CATALYZED AZIDATION AND AMINATION OF ALLYL ACETATES. SELECTIVE SYNTHESIS OF ALLYL AZIDES AND PRIMARY ALLYLAMINES
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Palladium catalyzed reaction of allyl acetates with azide ion gives allyl azides, which are readily converted into the corresponding primary allylamines upon treatment with PPh3/NaOH.
- Murahashi, Shun-Ichi,Tanigawa, Yoshio,Imada, Yasushi,Taniguchi, Yuki
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p. 227 - 230
(2007/10/02)
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