𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Cascade radical cyclisations of methylenecyclopropyl ketones—synthesis of bicyclo-[3.2.1]-octanes

✍ Scribed by Alexandre C. Saint-Dizier; Jeremy D. Kilburn


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
226 KB
Volume
43
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis


Samarium diiodide mediated cyclisation of methylenecyclopropyl ketones, readily prepared from b-ketoesters provides a simple route to bicyclo-[3.2.1]-octanes.


📜 SIMILAR VOLUMES


Radical cyclisations of methylenecyclopr
✍ David J Penfold; Kurt Pike; Anthony Genge; Mike Anson; John Kitteringham; Jeremy 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 105 KB

Addition of lithium bis(methylenecyclopropyl)cuprates to acetoxy azetidinones gives methylenecyclopropyl azetidinones, which can be converted to various radical cyclisation precursors. Attempted 4-exo cyclisation of 3 led only to reduced product, while cyclisation of 5, using CuCl/bipy, gave a carba

Cascade reactions with chiral michael ac
✍ Braun, Norbert A. ;Klein, Iris ;Spitzner, Dietrich ;Vogler, Bernhard ;Braun, Sie 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 602 KB

## Abstract Starting from the easily accesible chiral aldehyde 2, we obtained enantiomerically pure (__Z__)‐ and (__E__)‐α,‐chloro‐α,β‐unsaturated esters 4c in good yields by olefination reactions. (__Z__)‐and (__E__)‐4c were allowed to react with the kinetically controlled generated lithium dienol

NMR Study of Substituted Bicyclo[3.2.1]o
✍ John W. Blunt; Andrew Burritt; James M. Coxon; Peter J. Steel 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 English ⚖ 455 KB 👁 1 views

The 'H and I3C NMR spectra of six bromo-and methoxybicyclo[3.2.1]octanes were completely assigned. An axial bromine substituent at C-2 or C-4 results in a 5 ppm upfield shift of C-8 due to the gauche interaction. An equatorial bromine results in an upfield shift of similar magnitude on either C-6 (o

Synthesis of bicyclo[3.2.1]octanes by a
✍ James H. Rigby; Atul S. Kotnis 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 213 KB

The bicyclo[3.2.l]octane ring system is assembled by a three-step process featuring a thermally induced [4+2] cycloaddition followed by a 1,3benzodithiolium ion mediated cyclization onto an enol or silyl enol ether double bond. The bicyclo[3.2.l]octane carbon skeleton is a common structural subunit