65253-04-5Relevant articles and documents
Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary
Klepp, Julian,Podversnik, Harald,Puschnig, Johannes,Wallace, Andrew,Greatrex, Ben W.
supporting information, p. 3894 - 3903 (2019/06/18)
A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.
Method for Highly Enantioselective Ligation of Two Chiral C(sp3) Stereocenters
Bhimireddy, Eswar,Corey
supporting information, p. 11044 - 11047 (2017/08/22)
A method is described for the joining of two α-lithiated C(sp3) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at -90 °C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.
Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol
Crossley, Steven W. M.,Martinez, Ruben M.,Guevara-Zuluaga, Sebastián,Shenvi, Ryan A.
, p. 2620 - 2623 (2016/06/15)
Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.