10.1155/2012/457949
The research focuses on the development of a novel and efficient synthesis method for 1,2,3-thiadiazole and 1,2,3-diazaphosphole derivatives, which exhibit potential anticancer properties. The synthesis initiates with readily available starting materials like camphor and derivatives of acetophenone, and proceeds through a series of optimized steps to yield the target compounds. The study employs the Hurd-Mori and Lalezari methods for the preparation of 1,2,3-thiadiazole and 1,2,3-diazaphosphole derivatives, respectively. Various analytical techniques were utilized to characterize the synthesized compounds, including infrared spectroscopy (IR), mass spectrometry (MS), and proton nuclear magnetic resonance (1H-NMR). The synthesized compounds were then tested for their antibacterial and anticancer activities, with the anticancer activity being evaluated against a breast cancer cell line, and compared with the known anticancer drug Doxorubicin. The experiments involved the use of various ketones as reactants and the analysis of the synthesized compounds' structures and yields, as well as their biological activities.
10.1055/s-2004-822359
The research focuses on the development of a scandium-catalyzed enantioselective allylation method for the synthesis of homoallylic alcohols from aldehydes, using chiral allylboronates derived from camphor. The study explores the optimization of reaction conditions, the scope of substrates, synthetic applications, and mechanistic considerations. Key reactants include scandium triflate as a catalyst, various allyl-, methallyl-, and crotylboronates, and a range of aromatic, aliphatic, and propargylic aldehydes. The experiments utilized techniques such as NMR spectroscopy, HPLC, IR spectroscopy, optical rotation, and elemental analysis to analyze the products and determine their enantiomeric excess, diastereoselectivity, and other properties. The research successfully demonstrated high levels of diastereo- and enantioselectivity in the addition reactions and showcased the methodology's potential through gram-scale synthesis and a concise synthesis of the pheromone (4S)-2-methyloctan-4-ol.
10.1039/b911476a
The research focuses on developing a novel class of enantiopure carbene precursors based on camphor, an inexpensive and readily available chiral starting material. The purpose of this study is to explore the potential of these new carbene precursors in catalytic reactions, particularly in enantioselective transformations. The researchers synthesized several carbene precursors (5a–c) from camphor-derived diamine 3 using standard transformations with reagents such as MesCH2Cl, benzaldehyde, and anthracene-9-carbaldehyde. They also prepared salt 7 by reacting amine 6 with 2,4,6-trimethylbenzyl chloride. The carbenes derived from these precursors were tested in a formal [2+2] reaction of ketenes and aldehydes, yielding optically active β-lactones with good enantiomeric excess (ee) values, up to 92% ee in some cases. This study concludes that these new carbenes, with their unique structural features, can effectively catalyze enantioselective reactions, offering a promising avenue for asymmetric catalysis. Future work will involve exploring these carbenes as ligands in metal-catalyzed reactions.
10.1055/s-1988-27647
The research aims to synthesize chiral allenes from naturally occurring chiral ketones such as camphor or menthone, in order to obtain enantiomerically pure, sterically hindered allenes for investigating chiral induction in cycloadditions. The researchers used various chemical reactions and reagents, including the addition of dihalocarbene to double bonds, Wittig reactions, and reactions with lithium dimethylcuprate. They also employed techniques like 13C-NMR investigation and phase-transfer catalysis. The study found that some reactions were not trivial due to the difficulty in preparing exo-methylene compounds and the tendency of allenes to rearrange under certain conditions.
10.1016/S0957-4166(96)00463-6
The study focuses on the efficient synthesis of two camphor-derived chiral controllers, (2R-exo)-10-methylthio-2-bornanethiol (lb) and (2R-exo)-2,10-bis(methylthio)bornane (2), which have potential applications as ligands or chiral auxiliaries in asymmetric synthesis. The key starting material is (1S)-camphor-10-thiol (3), which is converted through a series of reactions involving benzoyl chloride, Lawesson's reagent, lithium aluminum hydride (LiAlH4), and diisobutylaluminum hydride (DIBAL-H) to achieve the desired chiral compounds. The study highlights the stereoselective reduction of thiones as a crucial method for introducing sulfur functionality in position 2 of the camphor-derived compounds. The synthesized compounds are characterized by various spectroscopic techniques, and their potential use in catalytic asymmetric hydroformylation and Pauson-Khand reactions is discussed.
F, 
Xn, 
Xi
F:Flammable;
