Download PDF
Synfacts 2014; 10(5): 0522
DOI: 10.1055/s-0033-1341219
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Generation of 3,3-Bis(silyl) Allyloxy Lithium for syn-Addition to Aldehydes and Ketones

Contributor(s):
Paul Knochel
,
Thomas Klatt
Lin X, Ye X, Sun X, Zhang Y, Gao L, Song Z * Sichuan University, Chengdu, P. R. of China
[1,5]-Anion Relay via Intramolecular Proton Transfer to Generate 3,3-Bis(silyl) Allyloxy Lithium: A Useful Scaffold for Syn-Addition to Aldehydes and Ketones.

Org. Lett. 2014;
16: 1084-1087
CrossrefSearch in Google Scholar
Further Information

Publication History

Publication Date:
17 April 2014 (online)

 
 PDF Download Permissions and Reprints

Key words

lithium - aldehydes - ketones

Significance

The authors describe a [1,5]-anion relay in 3,3-bis(silyl) benzyl enol ether. Deprotonation at the sterically more accessible benzylic position triggers an intramolecular proton transfer to generate the thermodynamically more stable 3,3-bis(silyl) allyloxy lithium.


#

Comment

In order to demonstrate the efficiency of this approach, the authors used a sequential anion relay process to perform a multicomponent reaction.


#
#


   Permissions and Reprints