N-Heterocyclic carbene-catalyzed diastereoselective synthesis of β-lactone-fused cyclopentanes using homoenolate annulation reaction.
نویسندگان
چکیده
NHC-catalyzed annulation of enals with 2-enoylpyridines or 2-enoylpyridine N-oxides leading to the diastereoselective synthesis of β-lactone-fused cyclopentanes is reported. The reaction proceeds via the generation of homoenolate equivalent intermediates and tolerates a broad range of functional groups.
منابع مشابه
N-heterocyclic carbene catalyzed annulation of benzofuran-2,3-diones and enals: a concise synthesis of spiro-bis-lactone.
The N-heterocyclic carbene catalyzed annulation of benzofuran-2,3-diones and enals via homoenolate intermediates is described. The reaction provided a direct and efficient method for the synthesis of spiro-bis-lactones. The ketone-carbonyl group annulated products and the ester-carbonyl group annulated products can be obtained as major products with good yields by convenient catalyst regulation...
متن کاملN-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.
The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate via single electron transfer was...
متن کاملN-heterocyclic carbene-catalyzed [4 + 1] annulation of phthalaldehyde and imines.
The diastereoselective synthesis of cis-2-amino-3-hydroxyindanones was realized by the N-heterocyclic carbene-catalyzed [4 + 1] annulation of phthalaldehyde and imines, which may involve a tandem aza-benzoin reaction and aldol reaction.
متن کاملEnantioselective synthesis of functionalized pyrazoles by NHC-catalyzed reaction of pyrazolones with α,β-unsaturated aldehydes.
The N-heterocyclic carbene (NHC)-organocatalyzed enantioselective annulation reaction of pyrazolones with α,β-unsaturated aldehydes proceeding via the chiral α,β-unsaturated acyl azolium intermediates under oxidative conditions is presented. The reaction afforded dihydropyranone-fused pyrazoles in moderate to good yields and good er values under operationally simple and base-free conditions.
متن کاملA highly regio- and stereoselective cascade annulation of enals and benzodi(enone)s catalyzed by N-heterocyclic carbenes.
The rapid catalytic construction of relatively complex molecules in a highly selective manner is an attractive goal in organic synthesis. In the area of N-heterocyclic carbene (NHC) catalysis, the unconventional NHC-mediated activation of enal compounds has led to a diverse set of new reactions, such as lactone and lactam formations, cycloaddition reactions, Michael reactions, and self-redox es...
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 51 46 شماره
صفحات -
تاریخ انتشار 2015