60112-29-0Relevant articles and documents
Trans-selective conversions of γ-hydroxy-α,β-alkynoic esters to γ-hydroxy-α,β-alkenoic esters
Meta, Christopher T.,Koide, Kazunori
, p. 1785 - 1787 (2007/10/03)
Matrix presented. γ-Hydroxy-α,β-acetylenic esters are used as precursors to prepare γ-hydroxy-α,β-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods a
A versatile preparation of alpha,beta-unsaturated lactones from homoallylic alcohols.
Keck,Li,Knutson
, p. 411 - 413 (2008/02/12)
[formula: see text] A new method for the synthesis of alpha,beta-unsaturated lactones from beta-acetoxy aldehydes by reaction with the lithium enolate of methyl acetate was developed. The reaction is relatively insensitive to structural changes in the ald
PREPARATION AND REACTIVITY OF FUNCIONALIZED ALKENYL-ZINC, -COPPER, AND -CHROMIUM ORGANOMETALLICS
Knochel, Paul,Rao, C. Janakiram
, p. 29 - 48 (2007/10/02)
β-Halogeno-α,β-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45 deg C, 1-4h).These funcionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97percent yield.The addition of a THF solution of CuCN*2LiCl to 2a affords the corresponding organocopper derivatives 2b which rect with electophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfuncional unsaturated carbonyl compounds in 71-95percent yield.The insertion of chromium (II) chloride to β-iodo and to some β-(p-tosyl)enones in DMF furnishes new funcionalized chromium (III) organometallics 2c which react with aldehydes providing γ-hydroxy unsaturated carbonyl derivatives in 40-91percent yield.The synthetic scope and the limitations of this methodology are discussed. Key words: funcionalized organozinc halides, alkenylchromium(III) compounds, copper-zinc organometallics.