Synthesis of Tetrahydropyrans through Formal [4+2] Cycloaddition
نویسندگان
چکیده
منابع مشابه
Preparation of highly substituted tetrahydropyrans via a metal assisted dipolar cycloaddition reaction.
A range of highly substituted tetrahydropyrans have been prepared by reaction of a donor-acceptor cyclobutane, where the donor is a metal-alkyne complex, with an aldehyde under Lewis acid conditions.
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An efficient method for the synthesis of 2,3,5,6-tetrasubstituted tetrahydropyrans has been developed from the reaction of aldehydes and ethyl 2-(1-hydroxyalkyl/hydroxy(phenyl)methyl)-5-methylhex-4-enoate using (3,5)-oxonium-ene reaction promoted by boron trifluoride etherate in good yields under mild conditions.
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(-)-Gephyrotoxin-223 was formally synthesized from chiral synthon 1 which has been chemoenzymatically synthesized in the presence of Candida Antartica lipase.
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Nucleophilic alkynes bearing sulfonamide, trimethylsilyl, or p-methoxyphenyl groups at the sp carbon reacted with 3-ethoxycyclobutanones to give formal [4 + 2] cycloadducts by activation with TiCl4. Reactions with 2-monoalkyl and 2-nonsubstituted 3-ethoxycyclobutanones gave phenol derivatives directly by benzannulation, while the use of 2,2-dimethyl-3-ethoxycyclobutanone gave the corresponding ...
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(R)-BINOL·SnCl(4) was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biological...
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ژورنال
عنوان ژورنال: Synfacts
سال: 2009
ISSN: 1861-1958,1861-194X
DOI: 10.1055/s-0029-1218254