title: Geminal bis(silyl) enal: a versatile scaffold for stereoselective synthesizing C3,O1-disilylated allylic alcohols based upon anion relay chemistry.
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.
authors: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.
authors: Linjie
authors: L
authors: Yan
authors: Xianwei
authors: X
authors: Sun
authors: Hongze
authors: H
authors: Li
authors: Zhenlei
authors: Z
authors: Song
authors: Zengjin
authors: Z
authors: Liu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D020005:Propanols; D012821:Silanes; C006463:allyl alcohol