387358-62-5Relevant academic research and scientific papers
Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
Breit, Bernhard,Schmidt, Johannes P.
supporting information, p. 23485 - 23490 (2020/10/29)
A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.
Visible-Light-Mediated Ring-Opening Strategy for the Regiospecific Allylation/Formylation of Cycloalkanols
Wang, Junlei,Huang, Binbin,Shi, Chengcheng,Yang, Chao,Xia, Wujiong
, p. 9696 - 9706 (2018/09/06)
Here we describe a straightforward and efficient approach for regiospecific introduction of an allyl group into cycloalkanol molecules employing a visible-light-mediated ring-opening strategy. A wide range of distally allylated or formylated ketones is fu
Rhodium-Catalyzed Asymmetric Conjugate Alkynylation/Aldol Cyclization Cascade for the Formation of α-Propargyl-β-hydroxyketones
Choo, Ken-Loon,Lautens, Mark
, p. 1380 - 1383 (2018/03/09)
A rhodium-catalyzed conjugate alkynylation/aldol cyclization cascade was developed. Densely functionalized cyclic α-propargyl-β-hydroxyketones were synthesized with simultaneous formation of a C(sp)-C(sp3) bond, a C(sp3)-C(sp3) bond, as well as three new contiguous stereocenters. The transformation was achieved with excellent enantio- and diastereoselectivities using BINAP as the ligand. The synthetic utility of the newly installed alkynyl moiety was exhibited by subjecting the products to an array of derivatizations.
Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine
Xie, Jian-Hua,Guo, Lu-Chuan,Yang, Xiao-Hui,Wang, Li-Xin,Zhou, Qi-Lin
, p. 4758 - 4761,4 (2012/12/13)
A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). T
Synthesis of hexahydrocyclopenta[c]furans by an intramolecular iron-catalyzed ring expansion reaction
Hilt, Gerhard,Bolze, Patrick,Heitbaum, Maja,Hasse, Katrin,Harms, Klaus,Massa, Werner
, p. 2018 - 2026 (2008/09/17)
The intramolecular iron-catalyzed ring expansion reaction of epoxyalkenes was investigated with a preformed iron(salen) [Fe(Salen)] complex. The formal insertion of the alkene into the epoxide generated hexahydrocyclopenta[c]furan derivatives in moderate to good yields and diastereoselectivities depending on other functional groups present in the starting materials. In addition, oxygen-tethered epoxyalkenes were used for the synthesis of lignan isomers. The scope and limitations of the Fe (Salen)-catalyzed process of the reaction are discussed.
