Organocatalytic Asymmetric Conjugate Addition of 3-Alkyl-Substituted Oxindoles to Vinyl Ketones
نویسندگان
چکیده
منابع مشابه
Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles.
An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.
متن کاملAsymmetric organocatalytic Michael addition of ketones to vinyl sulfone.
Highly enantioselective organocatalytic Michael addition of ketones to vinyl sulfone catalyzed by a cinchona alkaloid-derived primary amine is reported for the first time; the described synthetic methodology was applied to the synthesis of sodium cyclamate.
متن کاملOrganocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD)(2)PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented.
متن کاملOrganocatalytic enantioselective conjugate addition of ketones to isatylidine malononitriles.
An enantioselective Michael addition of ketones to alkylidenemalononitriles catalyzed by chiral primary amine I with (R)-5c as a co-catalyst in good yields (>90%) and with good enantioselectivities (85-96% ee) has been developed. The strategy has also been extended to a three-component version through a domino Knoevenagel/Michael sequence with similar or better outcomes.
متن کاملAsymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles.
Quinidine derivative (QD)(2)PYR was found to catalyze the asymmetric direct amination of unprotected prochiral 3-oxindole with DIAD to construct quaternary stereocenters at the C3 position with excellent enantioselectivity.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Bulletin of the Korean Chemical Society
سال: 2012
ISSN: 0253-2964
DOI: 10.5012/bkcs.2012.33.10.3171