Highly regio-, chemo- and diastereoselective synthesis of oxa-bridged spirocycles: a novel observation of reverse selectivity.
نویسندگان
چکیده
The reverse regio- and diastereoselectivities are observed between the reactions involving 5- and 6-membered-ring cyclic carbonyl ylide dipoles with alpha-methylene ketones. A mild catalytic route to synthesize spirocyclic systems with high regio-, chemo- and diastereoselectivities is described.
منابع مشابه
One-pot synthesis of nitrogen heterocycles initiated by regio- and diastereoselective carbon-carbon bond formation of bifunctional carbonyl compounds.
We report a one-pot synthesis of nitrogen heterocyclic compounds initiated by the allylation of the formyl group of bifunctional carbonyl compounds accompanying chemo-, regio-, and diastereoselective carbon-carbon bond formation in side chain moieties.
متن کاملSelective synthesis of functionalized, tertiary silanes by diastereoselective rearrangement-addition.
[reaction: see text] Treatment of hydroxy-substituted silyl epoxides with Grignard reagents induces a 1,2-carbon shift to reveal alpha-silyl aldehydes, which are trapped by highly diastereoselective addition reactions of the Grignard reagent. The starting epoxides are readily accessible from propargylic alcohols by regio- and diastereoselective hydrosilylation and epoxidation reactions. In addi...
متن کاملEfficient one-pot synthesis and characterization of 13-Acetyl-9-methyl-11-oxo-8-oxa-10,12-diazatricyclo [7.3.1.0^2,7] trideca-2,4,6-triene
An efficient and environmentally friendly procedure for one-pot synthesis of 13-acetyl-9-methyl-11-ox-8-oxa-10,12-diazatricyclo [7.3.1. ] trideca-2,4,6-triene from salicylaldehyde, acetylaceton and urea via Biginelli condensation and intramolecular Michael-addition by using magnesium bromide as an expensive and easily available catalyst under solvent-free condition is desired. The structural el...
متن کاملAn iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers.
A domino reaction has been developed for the synthesis of oxygen bridged bicyclic ethers through the coupling of 4-(2-hydroxyethyl)cyclohex-3-enols with aldehydes in the presence of 10 mol% of molecular iodine in dichloromethane at 25 °C. This method is highly diastereoselective affording the corresponding bicyclic ethers, i.e. octahydro-4a,7-epoxyisochromenes in good yields with high selectivi...
متن کاملStereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes.
Alkyl and aryl isothiocyanates and carbodiimides are effective substrates in (3+2) cycloadditions with N-sulfonyl-2-substituted aziridines and 2-phenylaziridine for the synthesis of iminothiazolidines and iminoimidazolidines. Additionally, the stereoselective (3+2) cycloaddition of N-H- and N-sulfonylaziridines with isothiocyanates can be accomplished, allowing for the synthesis of highly enant...
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 30 شماره
صفحات -
تاریخ انتشار 2005