51422-70-9Relevant articles and documents
Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes
Brown, M. Kevin,Houk, K. N.,Ni, Dongshun,Witherspoon, Brittany P.,Zhang, Hong,Zhou, Chen
supporting information, p. 11432 - 11439 (2020/05/18)
A method for the stereoselective [4+2]-cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N-protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C?B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.
Evaluation of the use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of secondary cyclohexenols
Sarotti, Ariel M.,Pisano, Pablo L.,Pellegrinet, Silvina C.
body text, p. 343 - 357 (2011/06/10)
The use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of isomeric mixtures of bicyclic and monocyclic secondary cyclohexenols was investigated. Synthesis, NMR and conformational analyses of the derivatives were performed and Gauge-Independent Atomic Orbital (GIAO) 1H NMR Boltzmann weighted average chemical shifts were computed. The studied methodology proved to be of practical value for most of the systems under study. ARKAT-USA, Inc.
Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels-Alder reaction
Zaidlewicz, Marek,Binkul, Jacek R.,Sokol, Wojciech
, p. 354 - 362 (2007/10/03)
Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels-Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation-mesylation-reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride produced pure olefins in good yields.