Aryl tert-butyl sulfoxide-promoted highly enantioselective addition of allyltrichlorosilane to aldehydes.
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.
Wang
Peng
P
National Engineering Research Center of Chiral Drugs and Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
Chen
Junmin
J
Cun
Linfeng
L
Deng
Jingen
J
Zhu
Jin
J
Liao
Jian
J
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013454:Sulfoxides / Q000737:chemistry*
D000447:Aldehydes; D000475:Alkenes; D012821:Silanes; D013454:Sulfoxides; C516132:allyltrichlorosilane