1135592-92-5Relevant academic research and scientific papers
Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations
Andler, Oliver,Kazmaier, Uli
supporting information, p. 8439 - 8444 (2021/10/25)
Allylzinc reagents are versatile nucleophiles that can be used in Matteson homologations. The linear substitution products are formed almost exclusively, and excellent E selectivities are observed in reactions of reagents with sterically demanding or aryl
Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol
Chen, Ming,Roush, William R.
supporting information; experimental part, p. 2706 - 2709 (2010/11/18)
(Figure presented) δ-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF 3·Et2O-promoted allylboration with α-Me-allylboronate 1. The origin of high (E)-selectivity is proposed
Enantioselective and catalytic method for α-crotylation of aldehydes with a kinetic self-refinement of stereochemistry
Malkov, Andrei V.,Kabeshov, Mikhail A.,Barlog, Maciej,Kocovsky, Pavel
supporting information; experimental part, p. 1570 - 1573 (2009/09/25)
A practical and catalytic approach towards enantioenriched homoallylic alcohols, using a two-step protocol combining a highly enantioselective Lewis base-catalyzed addition of crotyltrichlorosilanes to an auxiliary non-chiral aromatic aldehyde, was presen
Solid-phase synthesis of [5.5]-spiroketals
Sommer, Stefan,Kuehn, Marc,Waldmann, Herbert
supporting information; experimental part, p. 1736 - 1750 (2009/08/14)
An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramolecular hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochemistry. [5.5]-Spiroketals bearing an additional ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.
