A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality
نویسندگان
چکیده
منابع مشابه
An Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction
A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of LiOH.H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and i...
متن کاملStereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides
The Michael addition of dibenzylamine to (+)-tert-butyl perillate (3) and to (+)-tert-butyl phellandrate (6), derived from (S)-(-)-perillaldehyde (1), resulted in diastereomeric β-amino esters 7A-D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, tran...
متن کاملEnantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation.
An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities...
متن کاملDevelopment of ProPhenol Ligands for the Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-amino Esters
A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of di...
متن کاملan efficient protocol for the synthesis of carboacyclic nucleosides via aza-conjugate addition reaction
a new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of lioh.h2o (1.2-4.8 mol%) under microwave irradiation is described. this method affords the title compounds in good to excellent yields and in short reaction times.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Tetrahedron
سال: 2015
ISSN: 0040-4020
DOI: 10.1016/j.tet.2015.08.018