Highly stereoselective methylene transfers onto butanediacetal-protected chiral non-racemic sulfinyl imines using S-ylide technology.
نویسندگان
چکیده
Diastereomeric ratios of >95 : 5 were obtained when performing methylene transfers onto imines originating from d-mannitol and (S)-(-)-2-methyl-2-propane sulfinamide or ascorbic acid and (R)-(-)-2-methyl-2-propane sulfinamide.
منابع مشابه
(2S)-2-[(2S*,5R*,6R*)-5,6-Dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-1-[(S)-1,1-dimethylethylsulfonyl]aziridine
The reaction of a sulfur ylide with a chiral non-racemic sulfinyl imine afforded the desired aziridine in excellent yield and subsequent oxidation of the sulfinyl moiety dissolved in anhydrous dichloro-methane using a 75% aqueous solution of 3-chloro-per-oxy-benzoic acid afforded the title compound, C(14)H(27)NO(6)S. The configuration of the newly formed stereogenic center at the point of attac...
متن کاملTotal synthesis of siomycin A: construction of synthetic segments.
The five practical segments for the total synthesis of siomycin A, that is, the dehydropiperidine segment A (5), the pentapeptide segment B (3), the dihydroquinoline segment C (6), and the beta-phenylselenoalanine dipeptide segments D (7) and E (4), were synthesized. Segment A (5) was constructed by the coupling of the azomethine ylide and the chiral sulfinimine, followed by the stereoselective...
متن کاملThe asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines.
A new ylide-based protocol for the asymmetric aziridination of imines via methylene transfer has been developed involving the use of a simple chiral sulfonium salt and an organic strong base. A systematic study identified triisopropylphenyl sulfonylimines as optimal substrates for the process. Unexpectedly, hindered C2-symmetric sulfonyl salts incorporating bulky ethers at C-2 and C-5--which ha...
متن کاملPractical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.
Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aroma...
متن کاملHighly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and sulfides.
A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and allyl and propargyl sulfides by a double asymmetric induction approach that combines a chiral camphor sultam auxiliary and Cu(I) catalyst with chiral or achiral diimine ligands has been developed.
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 14 شماره
صفحات -
تاریخ انتشار 2009