119449-77-3Relevant academic research and scientific papers
The tethered aminohydroxylation (TA) of cyclic allylic carbamates
Donohoe, Timothy J.,Johnson, Peter D.,Cowley, Andrew,Keenan, Martine
, p. 12934 - 12935 (2002)
The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of
Further development of the tin-catalyzed transcarbamoylation reaction
Hasegawa, Tomoyuki,Ichikawa, Yoshiyasu,Masuda, Toshiya,Minami, Takahiro,Morishita, Yukinori,Ochi, Rika,Sato, Hiroshi
supporting information, p. 2373 - 2378 (2020/08/19)
Studies carried out to further develop tin-catalyzed trans-carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates.
An efficient synthesis of carbamates by tin-catalyzed transcarbamoylation reactions of primary and secondary alcohols
Ichikawa, Yoshiyasu,Morishita, Yukinori,Kusaba, Shuhei,Sakiyama, Naoto,Matsuda, Yasunori,Nakano, Keiji,Kotsuki, Hiyoshizo
experimental part, p. 1815 - 1818 (2010/10/05)
A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 ° C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance. Georg Thieme Verlag Stuttgart.
A new synthetic method for the preparation of amino sugars through an allyl cyanate-to-isocyanate rearrangement
Ichikawa, Yoshiyasu,Osada, Masafumi,Ohtani, Ikuko I.,Isobe, Minoru
, p. 1449 - 1455 (2007/10/03)
A new approach for the synthesis of amino sugars using an allyl cyanate-to-isocyanate rearrangement has been developed. The key feature in this method involves introduction of the nitrogen substituent into the pyranose framework by [3,3] sigmatropic rearrangement of an allyl cyanate. Subsequent functionalization of the allylamine moiety by either hydroxylation or cyclofunctionalization completes the synthesis of two amino sugars, D-perosamine and D-vicenisamine.
Novel, Regioselective Allylamine Construction; First Synthesis of Geranyllinaloisocyanide, a Diterpene from the Marine Sponge, Halichondria Sp.
Ichikawa, Yoshiyasu,Yamazaki, Masatugu,Isobe, Minoru
, p. 2429 - 2432 (2007/10/02)
The first synthesis of the diterpene, 3-isocyano-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene (geranyllinaloisocyanide, 1), has been achieved through an allyl cyanate-to-isocyanate rearrangement.The crucial step in this synthesis is in situ transformation of allyl isocyanates into stable allyl acetamides with trimethylaluminium.
STERIC CONTROL OF EPOXIDATION BY ALLYLIC AND HOMOALLYLIC CARBAMATE GROUPS
Kocovsky, Pavel
, p. 2475 - 2478 (2007/10/02)
Carbamoyloxy groups show syn-stereodirecting effect on epoxidation of allylic and homoallylic double bonds similar to that of hydroxy groups.Allylic carbamates 1c-1f, 4d, 6d and 6f and their homoallylic counterparts 8c-8e thus produce corresponding cis-epoxides as the major products on reaction with MCPBA.Mechanism of this steering is discussed.
