Stereoselective Ir(III)-catalyzed dimerization reaction of enynes: an entry to functionalized polyunsaturated and cyclic systems.

نویسندگان

  • Mehdi Ez-Zoubir
  • Florent Le Boucher d'Herouville
  • Jack A Brown
  • Virginie Ratovelomanana-Vidal
  • Véronique Michelet
چکیده

The Ir(III) complex [Ir(2)H(2)I(3)((rac)-Binap)(2)](+)I(-) efficiently promotes the selective dimerization of 1,6-, 1,7-enynes and functionalized alkynes. This catalytic process results in the formation of head-to-head isomers with (E)-stereoselectivity. Subsequent Rh-catalyzed cycloisomerization under reductive conditions led to the corresponding 1,2-dialkylidenecyclopentane derivatives.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion-oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed on the basis of mecha...

متن کامل

DABCO-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 کامل

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

A comprehensive study on the asymmetric gold-catalyzed cycloisomerization reaction of heteroatom tethered 1,6-enynes is described. The cycloisomerization reactions were conducted in the presence of the chiral cationic Au(I) catalyst consisting of (R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2) complex and silver salts (AgOTf or AgNTf(2)) in toluene under mild conditions to afford functionalized bic...

متن کامل

An Annulation Reaction for the Synthesis of Cross-Conjugated Triene-Containing Hydroindanes from Acyclic Precursors

In efforts directed toward the synthesis of seco-prezizaane sesquiterpenoids, a stereoselective annulation reaction has been developed between 4-hydroxy-1,6-enynes and TMS-alkynes that delivers cross-conjugated triene-containing hydroindanes. Contrary to previous reports, enyne substrates bearing two propargylic ethers enable the presumed organometallic intermediate to be trapped by double elim...

متن کامل

Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation

A new dimeric orthopalladated complex was synthesized via reaction of 2,3-dimethoxy benzaldehyde oxime with palladium chloride and lithium chloride in methanol as solvent and sodium acetate as base at room temperature. The catalytic activity of this dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(µ-Cl)]2 complex as an efficient, air, and moisture tolerant catalyst was investigated in Mizoroki–Heck cross ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Chemical communications

دوره 46 34  شماره 

صفحات  -

تاریخ انتشار 2010