Chiral lithium binaphtholate aqua complex as a highly effective asymmetric catalyst for cyanohydrin synthesis.
نویسندگان
چکیده
A highly enantioselective cyanohydrin synthesis with aromatic aldehydes using chiral lithium binaphtholate aqua or alcohol complexes has been developed and is a simple and inexpensive catalyst suitable for process chemistry to give gram-scale cyanohydrins successfully. Dramatic improvements in enantiomeric excess have been realized along with an interesting changeover in absolute stereochemistry of cyanohydrin product against the thoroughly "dry" catalytic systems.
منابع مشابه
An Efficient and One-pot Procedure for the Synthesis of Chiral Isoxazolidine via Catalytic Highly Enantioselective 1,3-dipolar cycloaddition
Synthesis of enantiomerically pure isoxazolidine via an asymmetric 1,3- dipolar cycloaddition reaction of nitrone with electron-deficient dipolarophile was described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendate bis(imine)–Cu(II)triflate complex as catalyst. The reaction mechanism is discussed on the basis of the assignment of t...
متن کاملThree-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition
The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(...
متن کاملThree-Component Procedure for the Synthesis Chiral Spirooxindolopyrrolizidines via Catalytic Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethineylides and 3-(2-Alkenoyl)-1,3-Oxazolidin-2-ones
The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imi...
متن کاملThree-Component Procedure for the Synthesis Chiral Spirooxindolopyrrolizidines via Catalytic Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethineylides and 3-(2-Alkenoyl)-1,3-Oxazolidin-2-ones
The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imi...
متن کاملDiastereoselective Lithiation of (h6- Arene)dicarbonyltriphenylphosphane Chromium(0) Oxazoline Complexes–Direct Preparation of Enantiopure Complexes Having Planar Chiral Fragments of Either Configuration**
Planar chiral h6-arene chromium(0) complexes are finding increasing application in the synthesis of enantioenriched compounds by serving as enantiopure starting materials or ligands for catalytic asymmetric processes.[1,2] Whereas early methods of generating enantiopure 1,2-disubstituted h6-arene chromium(0) complexes relied on resolution of racemates,[3] many methods have been developed recent...
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:
- Journal of the American Chemical Society
دوره 127 31 شماره
صفحات -
تاریخ انتشار 2005