Abstract
α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening) of the lithiated three-membered heterocycle by the lithio ether and then selective β-elimination of lithium alkoxide.
Highlights
Methods for the convergent generation of alkenes can be of significant utility in organic synthesis [1]
We report preliminary results on the latter strategy to form alkenes which possess an allylic heteroatom functionality (Scheme 2)
To examine the latter in the context of the current chemistry, α-methoxyhexyllithium derived from stannane 7 [14,15] was reacted with terminal epoxide 5, which gave the allylic alcohol 8 (79%, E/Z = 73:27, Scheme 4)
Summary
Methods for the convergent generation of alkenes can be of significant utility in organic synthesis [1]. Scheme 1: Dimerisation of α-lithio epoxides or aziridines [3,4,5]. To examine the latter in the context of the current chemistry, α-methoxyhexyllithium derived from stannane 7 [14,15] was reacted with terminal epoxide 5, which gave the allylic alcohol 8 (79%, E/Z = 73:27, Scheme 4). Scheme 2: Proposed eliminative cross-coupling of carbenoids to allylic alcohols (X = O) or allylic amines (X = NSO2t-Bu).
Sign-in/Register to view highlights & summary 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.
