Tetrahedron

Organotin-based bifunctional reagents: 4-chloro-2-lithio-1-botene and related substances: Methylenecyclopentane annotations. total synthesis of (±)-δ9 (12)- …

E Piers, V Karunaratne

Index: Piers, Edward; Karunaratne, Veranja Tetrahedron, 1989 , vol. 45, # 4 p. 1089 - 1104

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Citation Number: 58

Abstract

Transmetalatlon of 4-chloro-2-trimethylsCannyl-l-butene (4) with MeLi in tetrahydrofuran (THF) at-78° C affords 4-chloro-2-lithio-1-butene (5). At low temperatures (below approximately− 50 to− 60° C), 5 functions well as a bifunctional reagent. For example, reaction of 5 with aldehydes and ketones affords, depending on reaction conditions, chloro alcohols (eg 11, 14-18) or substituted 3-methyienetetrahydrofurans (eg 19-24). ...