Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: a facile access to α-methylene γ-lactams.
نویسندگان
چکیده
The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams.
منابع مشابه
An organocatalytic Michael-cyclization cascade of 4-oxa-α,β-unsaturated carboxylic acids with aldehydes: facile synthesis of chiral γ-lactols and trisubstituted γ-lactones.
An organocatalytic Michael-cyclization cascade of aldehydes with 4-oxa-α,β-unsaturated carboxylic acids has been developed, giving functionalized γ-lactols with high yields and enantioselectivities. The products could be easily transformed into complex trisubstituted γ-lactones and γ-lactams.
متن کاملHighly enantioselective organocatalytic Strecker reaction of cyclic N-acyl trifluoromethylketimines: synthesis of anti-HIV drug DPC 083.
A highly efficient, organocatalytic, enantioselective Strecker reaction of cyclic N-acyl ketimines was developed for the preparation of enantioenriched cyclic α-amino nitriles with a quaternary carbon stereocentre and anti-HIV drug DPC 083.
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 کاملDiastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
The cis- and trans-stereoselective radical additions to α-methylene-γ-alkyl- γ-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid.
متن کاملSulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester as a recyclable solid acid catalyst for the synthesis of α-amino nitriles
Sulfuric acid {[3-(3-silicapropyl)sulfanyl]propyl}ester (SASPSPE) is employed as a recyclable catalyst for the synthesis of α-amino nitriles. These syntheses were performed via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide under mild reaction conditions at room temperature. The catalyst could be recycled and reused several times without any loss of effi...
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:
- Organic & biomolecular chemistry
دوره 10 11 شماره
صفحات -
تاریخ انتشار 2012