88773-81-3Relevant articles and documents
Deoxygenative Divergent Synthesis: En Route to Quinic Acid Chirons
Holmstedt, Suvi,George, Lijo,Koivuporras, Alisa,Valkonen, Arto,Candeias, Nuno R.
supporting information, p. 8370 - 8375 (2020/11/02)
The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.
Undesirable deprotection of O-TBDMS groups by Pd/C-catalyzed hydrogenation and chemoselective hydrogenation using a Pd/C(en) catalyst
Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 2109 - 2114 (2007/10/03)
In general, O-TBDMS protective groups have been believed to be stable toward Pd/C-catalyzed hydrogenation conditions. In practice, however, frequent and unexpected loss of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. When a 10% Pd/C-ethylenediamine complex catalyst [10% Pd/C(en)] was used instead of 10% Pd/C, the undesirable problem was perfectly overcome and the chemoselective hydrogenation of reducible functionalities leaving intact the TBDMS protective group was achieved.
Catalysis by Solid Superacids; 19. Simplified and Improved Polymeric Perfluorinated Resin Sulfonic Acid (Nafion-H) Catalyzed Protection-Deprotection Reactions
Olah, George A.,Husain, Altaf,Singh, Brij P.
, p. 892 - 895 (2007/10/02)
-
