74630-48-1Relevant academic research and scientific papers
Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes
Pelter,Smith,Elgendy
, p. 7119 - 7132 (2007/10/02)
In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.
A Practical and Efficient Method for the Synthesis of β-Lactones
Danheiser, Rick L.,Nowick, James S.
, p. 1176 - 1185 (2007/10/02)
This paper describes a convenient one-step preparation of β-lactames based on the addition of thiol ester enolates to carbonyl compounds.Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce β-lactones in good to excellent yield.The new β-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns.In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded β-lactone diasteromers, and in some cases the reaction proceeds with excellent stereoselectivity.In conjunction with the stereospecific decarboxylation of β-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.
HINDERED ORGANOBORON GROUPS IN ORGANIC SYNTHESIS. 14. STEREOSELECTIVE SYNTHESIS OF ALKENES BY THE BORON-WITTIG REACTION USING ALIPHATIC ALDEHYDES
Pelter, Andrew,Smith, Keith,Elgendy, Said,Rowlands, Martin
, p. 5647 - 5650 (2007/10/02)
In the presence of HX, carbanions Mes2BCHLiR1 react with aliphatic aldehydes to give alkenes.The stereochemistry of product alkene depends upon the nature of HX.
