106623-23-8Relevant articles and documents
Asymmetric syntheses and applications of planar chiral hypervalent iodine(V) reagents with crown ether backbones
Yoshida, Yasushi,Kanashima, Yuto,Mino, Takashi,Sakamoto, Masami
, p. 3840 - 3849 (2019)
Novel optically active hypervalent iodine(V) reagents with planar chiral crown ether backbones were synthesized using the intramolecular Huisgen reaction as a key step and L-methyl lactate as the source of chirality. The relative configurations of these r
Asymmetric hydroxylative phenol dearomatization promoted by chiral binaphthylic and biphenylic iodanes
Bosset, Cyril,Coffinier, Romain,Peixoto, Philippe A.,El Assal, Mourad,Pouysegu, Laurent,Quideau, Stephane,Miqueu, Karinne,Sotiropoulos, Jean-Marc
supporting information, p. 9860 - 9864,5 (2014/10/15)
The long-standing quest for chiral hypervalent organoiodine compounds (i.e., iodanes) as metal-free reagents for asymmetric synthesis continues. Although remarkable progress has recently been made in organoiodine-catalyzed reactions using a terminal oxidant in stoichiometric amounts, there is still a significant need for "flaskable" chiral iodane reagents. Herein, we describe the synthesis of new iodobinaphthyls and iodobiphenyls, their successful and selective DMDO-mediated oxidation into either λ3- or λ5-iodanes, and the evaluation of their capacity to promote asymmetric hydroxylative phenol dearomatization (HPD) reactions. Most notably, a C2-symmetrical biphenylic λ5-iodane promoted the HPD-induced conversion of the monoterpene thymol into the corresponding ortho-quinol-based [4+2] cyclodimer (i.e., bis(thymol)) with enantiomeric excesses of up to 94 %.
Regio- and stereoselectivities in Diels-Alder cyclodimerizations of orthoquinonoid cyclohexa-2,4-dienones
Gagnepain, Julien,Méreau, Rapha?l,Dejugnac, Delphine,Léger, Jean-Michel,Castet, Frédéric,Deffieux, Denis,Pouységu, Laurent,Quideau, Stéphane
, p. 6493 - 6505 (2008/02/08)
The [4+2] cyclodimerization of cyclohexa-2,4-dienone derivatives of the orthoquinone monoketal and orthoquinol types has been the topic of numerous investigations over the last 50 years in the aim of rationalizing the extraordinary level of regio-, site-,