Studies on highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides.
نویسندگان
چکیده
A highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides in which proton served as the electrophile was reported. Through the X-ray diffraction study, it was concluded that the reaction may proceed via a 5-membered cyclic intermediate following by attack of the (-)OH at the sulfur atom.
منابع مشابه
Synthesis of 1,2-bisalkylidenecyclopentanes from 1,6-allenynes via stereoselective addition of nucleophiles to ruthenacyclopentenes.
Ruthenium-catalyzed cyclization of 1,6-allenynes occurs via the addition of heteroatom nucleophiles to ruthenacyclopentenes, providing functionalized 1,2-bisalkylidenecyclopentanes in a highly regio- and stereoselective manner.
متن کاملRegio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols.
A highly regio- and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-alpha,beta-d-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-beta-acetates or -carbonates in excellent yields. The 2-OH, 1-beta-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl tr...
متن کاملHighly stereoselective synthesis of (Z)-1,2-dihaloalkenes by a Pd-catalyzed hydrohalogenation of alkynyl halides.
An unprecedented Pd-catalyzed hydrohalogenation of alkynyl halides for the regio- and stereoselective synthesis of (Z)-1,2-dihaloalkenes has been realized using [(allyl)PdCl](2) as the catalyst and cis,cis-1,5-cyclooctadiene as the ligand. The advantages of this protocol are well illustrated by the assembly of trisubstituted (Z)-enynes and multifunctional benzenes via iterative cross-coupling r...
متن کاملStereoselective metabolism of dibenz(a,h)anthracene to trans-dihydrodiols and their activation to bacterial mutagens.
Dibenz(a,h)anthracene (DBA), a carcinogenic, polycyclic aromatic hydrocarbon ubiquitous in the environment, is metabolized by the hepatic microsomal fraction of immature Sprague-Dawley rats pretreated with Aroclor 1254 to 27 ethyl acetate-extractable metabolites. More than half of these metabolites (51%) consisted of trans-1,2-; -3,4-; and -5,6-dihydrodiols including their identified secondary ...
متن کاملDABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.
A DABCO-catalyzed highly regio- and stereoselective syn-1,4-bromolactonization of conjugated enynes was discovered. The 1,4-addition occurred selectively over 1,2-addition for most enynes. In contrast to anti 1,2-addition to alkenes, where two adjacent stereogenic centers are created, 1,4-addition across conjugated enynes can produce a stereogenic center and an axially chiral allene simultaneou...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 20 شماره
صفحات -
تاریخ انتشار 2010