Abstract
Reactions of α-sulfinyl carbanions, derived from p-tolyl sulfoxides bearing various alkyl groups, with various electrophiles were examined. The reaction of α-sulfinyl carbanions, derived from the β-silylethyl sulfoxides, with ketones or trimethyl phosphate, gave the syn products with high stereoselectivity. Interaction between the silicon in the trialkylsilyl group and the carbonyl oxygen in nucleophiles was postulated to stabilize the transition state, leading preferably to the syn diastereisomers. This novel silicon−oxygen interaction was supported by an MO calculation study using the MOPAC 93/PM3 and the Gaussian 94 Beche3LYP/3-21+G* methods.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
