Abstract
A synthesis of 2-substituted-1,3-dienes is reported which uses silicon as a control element: Eight aldehydes were converted into α-silyl ketones by treatment with trimethylsilylmethylmagnesium chloride and rapid Collins oxidation. Addition of vinylmagnesium bromide to the resulting α-silyl ketones, followed by Peterson elimination, gave a series of dienes. The route was used to make (4S)-3-methylene-t-[(phenylmethoxy)methoxy]pent-1-ene from (–)-ethyl lactate; low asymmetric induction was observed in the Diels–Alder reactions of this diene with diethyl fumarate and N-phenylmaleimide.
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 callSimilar Papers
More From: ChemInform
Disclaimer: 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.
