88773-81-3Relevant academic research and scientific papers
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.
Silylated cyclohexadienes in radical chain hydrosilylations
Amrein, Stephan,Studer, Armido
, p. 3559 - 3574 (2007/10/03)
A new method for the mild radical hydrosilylation of alkenes and alkynes is described. Silylated cyclohexadienes that can be readily prepared on large scale are used as radical hydrosilylating reagents. Nonactivated alkenes and alkynes are hydrosilylated in high yields. The reaction can be combined with C-C bond formation, as demonstrated for the preparation of silylated cycloalkanes from the corresponding dienes. Furthermore, radical hydrosilylations in combination with β-fragmentation reactions for the synthesis of allylsilanes and hydrosilylations of aldehydes and ketones providing protected alcohols can be readily performed by this strategy.
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.
The undesirable lability of tert-butyldimethylsilyl ethers under Pd/C- catalyzed hydrogenation conditions and solution of the problem by using a Pd/C(en) catalyst
Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 5711 - 5714 (2007/10/03)
While the frequent and unexpected loss of the TBDMS protective group of a variety of hydroxylic functions was demonstrated under neutral and mild hydrogenation conditions using 10% Pd/C, the undesirable problem was perfectly overcome by using a 10% Pd/C-ethylenediamine complex catalyst. (C) 2000 Elsevier Science Ltd.
