Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides.
نویسندگان
چکیده
A novel highly enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides catalysed by squaramide has been developed. This organocatalysed reaction proceeded well in high to excellent yields (up to >99%) to afford useful bioactive β-sulfated thioester derivatives with high enantioselectivities (up to 96% ee).
منابع مشابه
Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters.
The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) organocatalyst is described. The low acidity of the alkyl thiol pro-nucleophiles is overcome by the high Brønsted basicity of the catalyst and the chiral scaffold/thiourea hydrogen-bond donor moiety provides the required enant...
متن کاملSquaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes.
A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up...
متن کاملOrganocatalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β,γ-Unsaturated α-Ketoesters: An Access to Chiral Indolin-3-ones with Two Adjacent Tertiary Stereogenic Centers.
Asymmetric Michael addition of 1-acetylindolin-3-ones to β,γ-unsaturated α-ketoesters was investigated for the synthesis of chiral indolin-3-ones with two adjacent tertiary stereogenic centers. Under the catalysis of a chiral bifunctional squaramide derived from l-tert-leucine, a wide range of 1-acetylindolin-3-ones and β,γ-unsaturated α-ketoesters were well-tolerated in this transformation to ...
متن کاملEnantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters† †Electronic supplementary information (ESI) available: Experimental procedures, spectroscopic data, copies of 1H and 13C NMR spectra and HPLC and GC chromatograms. See DOI: 10.1039/c6sc02878k Click here for additional data file.
متن کامل
Squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to nitroalkenes.
An efficient chiral squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to nitroalkenes has been developed. This reaction afforded the chiral pyrazol-3-ol derivatives in high to excellent yields (up to >99%) with high enantioselectivities (up to 94% ee) for most substrates under very low catalyst loading (0.25 mol%). This catalytic asymmetric reaction provides valuable an...
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 12 10 شماره
صفحات -
تاریخ انتشار 2014