α-Bromodiazoacetamides – a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C–H insertion reactions

نویسندگان

  • Åsmund Kaupang
  • Tore Bonge-Hansen
چکیده

In this work, we introduce a new class of halodiazocarbonyl compounds, α-halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C-H insertions to produce α-halo-β-lactams. When carried out with α-bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α-halo-β-lactams, in some cases in excellent yields, depending on the ring size and substitution pattern of the cyclic amide side chains.

برای دانلود 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

Highly Enantio- and Diastereoselective Construction of 1,2-Disubstituted Cyclopentane Compounds by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]-Catalyzed C‒H Insertion Reactions of α-Diazo Esters

A highly enantioand diastereoselective intramolecular C–H insertion reaction of α-diazo esters has been achieved with the use of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] as a catalyst, providing exclusively cis-2-arylcyclopentane-1-carboxylates in up to 95% ee with no evidence of alkene formation.

متن کامل

α-Diazo-β-ketonitriles: uniquely reactive substrates for arene and alkene cyclopropanation.

An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor-acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. α-Diazo-β-ketonitriles al...

متن کامل

Intramolecular N–H insertion of -diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines

Along with the intramolecular C–H insertion reactions by carbenoids, intramolecular N–H insertion reactions of α-diazocarbonyl substrates catalyzed by metal complex have received considerable attention in recent years. This type of insertion reaction has been shown to be a mild and efficient route to 4-, 5-, and 6-membered aza rings. A frequently cited example of this powerful approach is the M...

متن کامل

Catalyst-free intramolecular formal carbon insertion into σ-C-C bonds: a new approach toward phenanthrols and naphthols.

The different reactivity of two kinds of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom-containing analogues. Key to this highly efficient and robust methodology is the catalyst-free intramolecular formal diazo carbon insertion of N-tosylhydrazones into keto C-C bonds.

متن کامل

Diastereoselective intermolecular O H insertions by Cu(II)-mediated carbenoids derived from phenyldiazoacetamide

The diastereoselective insertion into carboxylic O H bonds was investigated with camphorsultam as a chiral auxiliary, and moderate to good selectivity was achieved. © 2001 Elsevier Science Ltd. All rights reserved. Along with the well established intramolecular C H insertion reactions by Rh(II)-mediated carbenoids, there has been considerable attention directed to the corresponding insertion in...

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

برای دانلود 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

عنوان ژورنال:

دوره 9  شماره 

صفحات  -

تاریخ انتشار 2013