Tributyltin hydride-mediated radical cyclisation reactions: efficient construction of multiply substituted cyclopentanes.
نویسندگان
چکیده
The nBu(3)SnH-mediated cyclisation reactions of allylic-allylic alkylation products of alpha,alpha-dicyanoalkenes and Morita-Baylis-Hillman (MBH) carbonates of methyl vinyl ketone (MVK) have been investigated. Cyclopentane derivatives bearing multiple substituents were efficiently prepared with moderate to excellent diastereoselectivity.
منابع مشابه
Enantioselective radical cyclisation reactions of 4-substituted quinolones mediated by a chiral template.
Six 4-substituted quinolones 6-8, which bear an ω-iodoalkyl chain, were prepared and subjected to reductive radical cyclisation conditions employing BEt(3)/O(2) as the initiator and either Bu(3)SnH or TMS(3)SiH as hydride source. 4-(4-Iodobutyl)-quinolone (6a) and 4-(3-iodopropylthio)-quinolone (8a) gave the respective 6-endo-cyclisation products in good yields. 4-(3,3-Dimethyl-4-iodobutyl)-qui...
متن کاملDenitration of Nitroesters with Tributyltin Hydride in the Presence of Azobisisobutyronitrile (AIBN)
Among the different reducing agents tributyltin hydride was found to be a powerful reducing agent for the denitration of a series of tertiary and secondary nitroesters. The organotin residues removed from the crude product using saturated potassium fluoride solution. The yield of the reactions was 62-98%.
متن کاملTotal syntheses of telisatin A, telisatin B and lettowianthine.
Treatment of 1-(2-bromoarylmethyl)-3,4-dihydroisoquinolines with oxalyl chloride and triethylamine gave 1-(2-bromophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione derivatives, for example, 1-(2-bromophenyl)-5,6-dihydro-8,9-dimethoxypyrrolo[2,1-a]isoquinoline-2,3-dione. Radical cyclisation of these derivatives with tributyltin hydride and 1,1-azobis(cyclohexanecarbonitrile) afforded telis...
متن کاملRadical carbonylations using a continuous microflow system
Radical-based carbonylation reactions of alkyl halides were conducted in a microflow reactor under pressurized carbon monoxide gas. Good to excellent yields of carbonylated products were obtained via radical formylation, carbonylative cyclization and three-component coupling reactions, using tributyltin hydride or TTMSS as a radical mediator.
متن کاملA new approach for the generation and reaction of organotin hydrides: the development of reactions catalytic in Tin
Organotin compounds are versatile reagents in organic chemistry.1 Among the most commonly used tin reagents is tributyltin hydride.2 One of tributyltin hydride’s major applications is in free-radical reactions3 such as dehalogenations of alkyl, vinyl, or aryl halides, often followed by intraor intermolecular C-C coupling. These chain reactions allow the formation of quite complex ring systems a...
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 8 12 شماره
صفحات -
تاریخ انتشار 2010