A Phosphoramide Catalyzed Asymmetric Diels-Alder Reaction
نویسندگان
چکیده
منابع مشابه
Asymmetric hetero-Diels-Alder reaction catalyzed by dirhodium(II) carboxamidates.
Chiral dirhodium(II) carboxamidates are highly efficient catalysts for reactions between a variety of aldehydes and activated dienes. Catalyst loadings as low at 0.01 mol % have been realized with enantioselectivities up to 97%. Kinetic investigations reveal a pronounced electronic influence on the rate of the hetero-Diels-Alder reaction with a Hammett rho value of +1.9 (versus sigma(+)). Inhib...
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The aqueous Diels-Alder reaction of 1,3-cyclohexadiene with 1,4-benzoquinone was compared and contrasted to the same reaction catalyzed with Flextyl P, a novel Ti(IV) performance catalyst. The catalyst improved conversion by 22% versus the uncatalyzed reaction and represents a rare example of a Ti(IV) catalyzed Diels-Alder reaction in water.
متن کاملAsymmetric Catalysis of Diels–Alder Reaction
The Diels–Alder (DA) reaction (or diene synthesis) between a diene and a dienophile generates two s bonds stereoselectively and up to four chiral centers in a single step to afford six-membered cyclic compounds. This cycloaddition reaction named after Professor Otto Paul Hermann Diels (1876–1954) and his student Kurt Alder (1902–1958) was discovered in 1928 during studies on the reaction of b...
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A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels-Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective...
متن کاملDesign of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction.
A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels-Alder reaction of alpha,beta-unsaturated ketone with silyloxydiene was demonstrated using this chiral Brønsted acid catalyst.
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ژورنال
عنوان ژورنال: Synfacts
سال: 2006
ISSN: 1861-1958,1861-194X
DOI: 10.1055/s-2006-949228