- The tethered aminohydroxylation (TA) of cyclic allylic carbamates
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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
- Donohoe, Timothy J.,Johnson, Peter D.,Cowley, Andrew,Keenan, Martine
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- Further development of the tin-catalyzed transcarbamoylation reaction
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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.
- Hasegawa, Tomoyuki,Ichikawa, Yoshiyasu,Masuda, Toshiya,Minami, Takahiro,Morishita, Yukinori,Ochi, Rika,Sato, Hiroshi
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supporting information
p. 2373 - 2378
(2020/08/19)
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- An efficient synthesis of carbamates by tin-catalyzed transcarbamoylation reactions of primary and secondary alcohols
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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.
- Ichikawa, Yoshiyasu,Morishita, Yukinori,Kusaba, Shuhei,Sakiyama, Naoto,Matsuda, Yasunori,Nakano, Keiji,Kotsuki, Hiyoshizo
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experimental part
p. 1815 - 1818
(2010/10/05)
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- A new synthetic method for the preparation of amino sugars through an allyl cyanate-to-isocyanate rearrangement
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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.
- Ichikawa, Yoshiyasu,Osada, Masafumi,Ohtani, Ikuko I.,Isobe, Minoru
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p. 1449 - 1455
(2007/10/03)
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- Novel, Regioselective Allylamine Construction; First Synthesis of Geranyllinaloisocyanide, a Diterpene from the Marine Sponge, Halichondria Sp.
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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.
- Ichikawa, Yoshiyasu,Yamazaki, Masatugu,Isobe, Minoru
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p. 2429 - 2432
(2007/10/02)
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- STERIC CONTROL OF EPOXIDATION BY ALLYLIC AND HOMOALLYLIC CARBAMATE GROUPS
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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.
- Kocovsky, Pavel
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p. 2475 - 2478
(2007/10/02)
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