Geminal bis(silyl) enal: a versatile scaffold for stereoselective synthesizing C3,O1-disilylated allylic alcohols based upon anion relay chemistry.

Authors :: Yan L
Sun X
Li H
Song Z
Liu Z
Source :: Organic letters [Org Lett] 2013 Mar 01; Vol. 15 (5), pp. 1104-7. Date of Electronic Publication: 2013 Feb 15.
Publication Year :: 2013
Abstract: Geminal bis(silyl) enal 2a is shown to be a useful scaffold for anion relay chemistry (ARC) aimed at the stereoselective synthesis of C(3),O(1)-disilylated allylic alcohols. The ARC reaction is initiated by the addition of an alkyllithium to the aldehyde and features a CuCN-promoted C(sp2)-to-O 1,4-silyl migration to generate a vinylcuprate that reacts with activated electrophiles.

Subjects :: Aldehydes chemistry
Combinatorial Chemistry Techniques
Molecular Structure
Propanols chemistry
Stereoisomerism
Propanols chemical synthesis
Silanes chemical synthesis
Silanes chemistry

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