605656-97-1Relevant academic research and scientific papers
Allene: As small in size as versatile in synthesis. A general scope of its use-fulness as a C3-synthon for carbocyclic annulations
Barbero, Asuncion,Pulido, Francisco J.
, p. 779 - 785 (2007/10/03)
Allenes react with silylcuprates leading to allyl- or vinylsilanes depending on the structure of the allene and the nature of the silylcuprate. The silyl group used and temperature conditions can also influence the final outcome. Reversibility is a common
New evidence on the regiochemistry of the tert-butyldiphenylsilylcupration of allene using the silylcuprate or silylcopper reagent
Cuadrado, Purificación,González-Nogal, Ana M.,Sánchez, Alicia,Sarmentero, M. Angeles
, p. 5855 - 5859 (2007/10/03)
The regiochemistry in the tert-butyldiphenylsilylcupration of the allene depends on the temperature and also on the nature of the electrophile. Thus, the intermediate generated by addition of the silylcuprate at -78°C reacted with electrophiles to give allylsilanes, except with oxo compounds which afforded vinylsilanes. On the other hand, the silylcopper reagent was added at -40°C leading, in all cases, to the corresponding allylsilanes. When enones were used as electrophile the vinylsilanes were the 1,2-addition products and the allylsilanes those from 1,4-addition. These functionalized vinyl or allyl tert-butyldiphenylsilanes are interesting synthons for the preparation of conjugated tert-butyldiphenylsilyltrienes and functionalized exocyclic alkylidenecyclopentenes.
Functionalised allylsilanes from silylcopper reagents and allene. A useful strategy for cyclopentane annulations
Barbero, Asuncion,García, Carlos,Pulido, Francisco J.
, p. 2739 - 2751 (2007/10/03)
Silylcupration of allene using phenyldimethylsilylcopper or t- butyldiphenylsilylcopper followed by reaction with α,β-unsaturated acyl chlorides, aldehydes or ketones affords allylsilane-containing divinyl ketones and oxoallylsilanes, respectively. They u
