Enantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions.
نویسندگان
چکیده
A highly enantioselective construction of delta- and gamma-lactone[2,3-b]piperidine skeletons was accomplished by tandem aza-Diels-Alder reaction-hemiacetal formation-oxidation from N-Tos-1-aza-1,3-butadienes and aliphatic dialdehydes.
منابع مشابه
Highly enantioselective [4+2] annulation via organocatalytic Mannich-reductive cyclization: one-pot synthesis of functionalized piperidines.
A new method for one-pot synthesis of 2,3-substituted piperidine from N-PMP aldimine and aqueous glutaraldehyde via formal [4+2] cycloaddition is reported. This reaction involves organocatalytic direct Mannich reaction-reductive cyclization with high yields (up to 90%) and excellent enantioselectivities (up to >99%). The practicability of this method is also shown at a gram scale as well as thr...
متن کاملOrganocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines
Enantioselective organocatalysis has become a field of central importance within asymmetric chemical synthesis and appears to be efficient approach toward the construction of complex chiral molecules from simple achiral materials in one-pot transformations under mild conditions with high stereocontrol. This review addresses the most significant synthetic methods reported on chiral-amine-catalyz...
متن کاملEnantioselective synthesis of allenamides via sulfimide [2,3]-sigmatropic rearrangement.
Chiral allenamides are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of propargylic sulfimides. The required branched propargylic sulfides are prepared by an enantioselective organocatalytic aldehyde alpha-sulfenylation followed by Corey-Fuchs alkynylation.
متن کاملEnantioselective organocatalytic partial transfer hydrogenation of lactone-fused quinolines.
The first enantioselective synthesis of 4-aza-podophyllotoxin derivatives by partial transfer hydrogenation of lactone-fused quinolines was achieved using a chiral Brønsted acid catalyst. This reaction was extended to a large scope of substrates with good yields and enantioselectivities.
متن کاملOne-pot Synthesis of Pyrono [2,3] Quinoline via the Tandem Cyclization of Algar-Flyn-Oyamanda Reactions
A new and imaginative technique for the synthesis of substituted pyranoquinoline via Algar Flyn Oyamanda oxidation cyclization approach has been achieved by hydrogen peroxide and sodium hydroxide catalyzed of quinoline chalcone with intramolecular cyclization to formed pyranoquinoline. In this reaction, two new C-C bonds were formed in a one step with high atom economy. The possible reaction pa...
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 8 4 شماره
صفحات -
تاریخ انتشار 2010