1192110-03-4Relevant articles and documents
Stereoselective synthesis of isoindolinones and tert-butyl sulfoxides
Kaw?cki, Robert,Stańczyk, Wojciech,Jaglińska, Agnieszka
, p. 578 - 584 (2017/12/28)
A reaction of Grignard reagents with an optically pure N-sulfinylimine derived from methyl 2-formylbenzoate yields enantioenriched isoindolinones and tert-butyl sulfoxides. The products are formed by the addition of the nucleophile to N-sulfinylimine followed by cyclization to form N-tert-butylsulfinylisoindolinone, which readily undergoes substitution with a second equivalent of Grignard reagent. The reaction can be carried out in dichloromethane at room temperature or at elevated temperatures without any loss of stereoselectivity. The use of nucleophiles other than Grignard reagents has also been investigated.
Aryl tert-butyl sulfoxide-promoted highly enantioselective addition of allyltrichlorosilane to aldehydes
Wang, Peng,Chen, Junmin,Cun, Linfeng,Deng, Jingen,Zhu, Jin,Liao, Jian
experimental part, p. 3741 - 3747 (2009/10/24)
A series of enantiomerically pure mono- and bis-aryl tert-butyl sulfoxides were synthesised to promote the enantioselective allylation of aldehydes with allyltrichlorosilane. Moderate to good yields and modest to high enantioselectivities were achieved. The absence of nonlinear effect, spacer effect, promoter loading and concentration effect indicate that only one molecule of aryl tert-butyl sulfoxide is involved in the stereodetermining step.
