187869-61-0Relevant articles and documents
A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation
Cooper, Stephen P.,Booker-Milburn, Kevin I.
supporting information, p. 6496 - 6500 (2015/06/02)
Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).
Nickel(0)-promoted carboxylation of allenamides with carbon dioxide via a nickelalactone intermediate
Saito, Nozomi,Sugimura, Yasuyuki,Sato, Yoshihiro
supporting information, p. 736 - 740 (2014/04/03)
Nickel(0)-promoted carboxylation of N-allenylamides (allenamides) with carbon dioxide proceeded via a nickelalactone intermediate to give β-amino acid derivatives. It was also found that the regioselectivity at the oxidative addition stage was strongly af
Direct intramolecular catalytic enantioselective alkylation of oxazolidinone bromoalkanoate imides
De Rycke, Nicolas,St Denis, Jeffrey D.,Hughes, Jonathan M. E.,Rosadiuk, Kristopher A.,Gleason, James L.
supporting information, p. 2802 - 2805 (2015/01/08)
Bromoalkanoate imides undergo intramolecular alkylation to form cyclopentane carboximides using catalytic amounts of magnesium bromide in the presence of DBU. Addition of PyBox ligands affords alkylation products with moderate enantioselectivity.
Total synthesis of ceratopicanol through tandem cycloaddition reaction of a linear substrate
Lee, Sang-Shin,Kim, Won-Yeob,Lee, Hee-Yoon
, p. 2450 - 2456,7 (2020/08/24)
Total synthesis of ceratopicanol (1) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary c
Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins
Hodgson, David M.,Ying, Kit Chung,Nuzzo, Irene,Freixas, Gloria,Kulikiewicz, Krystyna K.,Cleator, Ed,Paris, Jean-Marc
, p. 4456 - 4462 (2008/02/02)
Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]-hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]-hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-β-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.
13. Synthesis and Odor of Chiral Partial Structures of Khusimone
Spreitzer, Helmut,Pichler, Andrea,Holzer, Wolfgang,Toth, Irene,Zuchart, Bettina
, p. 139 - 145 (2007/10/03)
Khusimone (1), one of the main odor-donating compounds of vetiver oil is subject of the following study on structure/odor relationship. The omittance of the ethano bridge of the tricyclic khusimone leads to a bicyclic system. The stereoselective approach
