Lewis acid mediated additions of 1,3-bis(silyl)propenes to glyoxyamide: An efficient approach to the synthesis of highly functionalized allylsilanes

ORGN 19

Peter Somfai, somfai@kth.se and Pavel Tuzina, tuzina@kth.se. KTH Chemistry, Organic Chemistry, Royal Institute of Technology, Teknikringen 36, 100 44 Stockholm, Sweden
Nucleophilic carbonyl addition reactions have served as a versatile tool in organic synthesis for stereoselective C-C bond formation. Nevertheless, no examples of the addition of 1,3-bis(silyl)propenes (1) to chelating carbonyl substrates have been reported. Recently we have developed an efficient synthetic protocol for addition of 1,3-bis(silyl)propene 1 to glyoxyamide 2 to produce a range of α-silyloxyallylsilanes (3) in good yields. Insight into the reaction mechanism is also presented.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008