60886-80-8Relevant articles and documents
(+)-camphorsulfonylimine
Chakraborty, Arindam,Ray, Jayanta Kumar,Chinnakali, Kandasamy,Razak, Ibrahim Abdul,Fun, Hoong-Kun
, p. 1725 - 1726 (1997)
The norbornane ring system in the title molecule, 8, 8-dimethy 1-3, 3a, 4,5,6,7-hexahydro-3a, 6-methanobenz[c]isothiazole S,S-dioxide, C10H15NO2S, is regular with normal bond lengths and angles. The bridgehead bond angle is 92.5 (2)°. The five-membered ring of the sulfonylimine moiety adopts a flattened envelope conformation. The crystal structure is stabilized by weak C - H. . .O hydrogen bonds.
Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds
Carvalho, M. Fernanda N. N.,Herrmann, Rudolf,Wagner, Gabriele
, p. 1230 - 1238 (2017/07/03)
Compounds containing two alkyne groups in close vicinity at the rigid skeleton of camphorsulfonamide show unique reactivities when treated with electrophiles or catalytic amounts of platinum(II). The formed product structures depend not only on the reagents used but also on the substituents attached to the triple bonds. Cycloisomerisations with perfect atom economy lead to polycyclic heterocycles that resemble to some extent the AB ring system of paclitaxel. Herein, we present practical synthetic methods for the selective synthesis of precursor dialkynes bearing different substituents (alkyl, aryl) at the triple bonds, based on ketals or an imine as protecting groups. We show for isomeric dialkynes that the reaction cascade induced by Pt(II) includes ring annulation, sulphur reduction, and ring enlargement. One isomeric dialkyne additionally allows for the isolation of a pentacyclic compound lacking the ring enlargement step, which we have proposed as a potential intermediate in the catalytic cycle.
Influence of norbornanone substituents on both the Wagner-Meerwein skeletal rearrangements under sulfonation conditions and the diastereoselectivity of the corresponding N,N′-bis-fumaroyl sultams in uncatalyzed Diels-Alder cycloadditions to cyclopenta-1,3-diene
Pia?tek, Anna,Chapuis, Christian
, p. 4247 - 4249 (2013/07/26)
The Wagner-Meerwein domino rearrangement of norbornanone skeletons, under sulfonation conditions, is strongly influenced by the absence of a gem-dimethyl moiety at C(7). As a result, sulfonation at C(10) is less efficient due to a divergent pathway in the intermediate double bond formation and/or isomerization. Furthermore, the absence of such a gem-dimethyl moiety in the corresponding norbornane[10,2]sultam derivatives, sterically influences the orientation of the SO(1) and SO(2) substituents, hence on the π-facial steric shielding of the thermodynamically more stable anti-s-cis N-alkenoyl dienophiles. As a consequence, their diastereoselective [4+2] cycloadditions to cyclopenta-1,3-diene, under nonchelating conditions, are not as efficient due to a less pseudo axial SO(1) and the consequent loss of pseudo C 2-symmetry.
