N-Heterocyclic carbene-catalyzed [3 + 2] annulation of bromoenals with 3-aminooxindoles: highly enantioselective synthesis of spirocyclic oxindolo-γ-lactams.
نویسندگان
چکیده
The chiral N-heterocyclic carbene-catalyzed [3 + 2] annulation of α-bromoenals and 3-aminooxindoles was developed, giving the corresponding spirocyclic oxindolo-γ-lactams in good yields with high diastereoselectivities and enantioselectivities.
منابع مشابه
Highly 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 کاملHighly diastereo- and enantioselective NHC-catalyzed [3+2] annulation of enals and isatins.
The chiral N-heterocyclic carbene bearing a proximal hydroxy group derived from L-pyroglutamic acid was found to be an efficient catalyst for the [3+2] annulation of enals and isatins to give the corresponding spirocyclic oxindolo-γ-butyrolactones in good yield with good diastereo- and enantioselectivities.
متن کاملN-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals.
An N-heterocyclic carbene catalyzed enantioselective [3+3] annulation of benzothiazolyl acetates with 2-bromoenals has been developed. The protocol provides a direct asymmetric synthesis of dihydro-1H-benzothiazolopyridinones in good to very good yields and medium ee values. In many cases, the virtually enantiopure heterocycles are available through a single recrystallization (99% ee).
متن کاملN-Heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals with hydrazones: highly enantioselective synthesis of dihydropyridazones.
The N-heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals and hydrazones is developed to give the corresponding chiral 4,5-dihydropyridazones in good yields with excellent enantioselectivities.
متن کاملN-Heterocyclic carbene-catalyzed [3+3] cyclocondensation of bromoenals with aldimines: highly enantioselective synthesis of dihydropyridinones.
The N-heterocyclic carbene-catalyzed [3+3] cyclocondensation of bromoenals and aldimines was developed to give the corresponding dihydropyridinones in good yields with excellent enantioselectivities.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 14 6 شماره
صفحات -
تاریخ انتشار 2016