Ru-catalyzed highly chemo- and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters under neutral conditions.
نویسندگان
چکیده
Finely-tuned ruthenium-catalyzed highly chemoselective and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters at the carbonyl group was achieved under neutral reaction conditions (ee up to 97%). Both olefin and alkenyl halogen moieties, which are labile under hydrogenation conditions, remained untouched during the reaction.
منابع مشابه
Copper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
A copper-catalyzed cascade reaction of α,β-unsaturated esters with keto esters is reported. It features a copper-catalyzed reductive aldolization followed by a lactonization. This method provides a facile approach to prepare γ-carboxymethyl-γ-lactones and δ-carboxymethyl-δ-lactones under mild reaction conditions.
متن کاملHighly efficient asymmetric hydrogenation of cyano-substituted acrylate esters for synthesis of chiral γ-lactams and amino acids.
A highly efficient and enantioselective synthesis of γ-lactams and γ-amino acids by Rh-catalyzed asymmetric hydrogenation has been developed. Using the Rh-(S,S)-f-spiroPhos complex, under mild conditions a wide range of 3-cyano acrylate esters including both E and Z-isomers and β-cyano-α-aryl-α,β-unsaturated ketones were first hydrogenated with excellent enantioselectivities (up to 98% ee) and ...
متن کاملHighly Enantioselective Hydrogenation of a-Keto Esters Catalyzed by Ru-Tunephos Complexes Highly Enantioselective Hydrogenation of a-Keto Esters
SYNLETT 2006, No. 8, pp 1169–117215.05.2006 Advanced online publication: 10.03.2006 DOI: 10.1055/s-2006-932461; Art ID: W30605ST © Georg Thieme Verlag Stuttgart · New York Abstract: Various enantiomerically pure a-hydroxy esters were synthesized by asymmetric hydrogenation of a-keto esters catalyzed by Ru-Cn-Tunephos complex. Up to 97.1% ee has been achieved for both a-aryl and a-alkyl substitu...
متن کاملDABCO-catalyzed regioselective cyclization reactions of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters.
Highly efficient DABCO-catalyzed [4 + 2] cycloaddition of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters gives the corresponding highly functionalized tetrahydropyran and dihydropyran derivatives in good to excellent yields and moderate to good regioselectivities under mild conditions.
متن کاملAcid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO3.
A series of acid-labile, optically pure ε-substituted δ-ketal-β-hydroxy esters were obtained by a Ru-SunPhos catalyzed asymmetric hydrogenation of the corresponding ε-substituted δ-ketal-β-keto esters. CaCO(3) played a dual role in the hydrogenation reaction--removing the acid generated during the formation of the catalyst and maintaining the activity of the catalyst.
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 48 43 شماره
صفحات -
تاریخ انتشار 2012