Highly enantioselective aza-Henry reaction with isatin N-Boc ketimines.
نویسندگان
چکیده
A highly enantioselective aza-Henry reaction with isatin N-Boc ketimines using a Cu(II)-BOX complex as a catalyst is described. The reaction, which does not require protection of the N1 atom, provides the corresponding nitroamines bearing a quaternary stereocentre with high yields and enantiomeric excesses (up to 99.9%).
منابع مشابه
The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids.
The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported. In general, derivatives of substituted 3-amino-2-oxindoles were obtained with excellent enantioselectivities and high yields.
متن کاملHighly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.
An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).
متن کاملN-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles.
A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.
متن کاملOrganocatalytic asymmetric cyanation of isatin derived N-Boc ketoimines.
We report the first catalytic asymmetric cyanation of N-Boc ketoimines, which enables highly enantioselective synthesis of oxindole based α-amino nitriles. An unprecedented tandem aza-Wittig/Strecker reaction is also developed, emerging as a promising strategy for the catalytic asymmetric cyanation of ketoimines formed in situ from achiral ketones.
متن کاملMaleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles.
A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 66 شماره
صفحات -
تاریخ انتشار 2014