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Bridgehead Lithiated 9-Oxabispidines

Title data

Breuning, Matthias ; Steiner, Melanie ; Hein, David ; Hörl, Christian ; Maier, Philipp:
Bridgehead Lithiated 9-Oxabispidines.
In: Synlett. (2009) Issue 17 . - pp. 2749-2754.
ISSN 1437-2096
DOI: https://doi.org/10.1055/s-0029-1217999

Abstract in another language

Bi- and tricyclic 9-oxabispidines are smoothly deprotonated at -78 ˚C by s-BuLi at one of the bridgehead carbon atoms to give α-lithio ethers, which were trapped with electrophiles in good yields. Rearrangements to ring-contracted N,O-acetals occurred upon warming in the absence of an electrophile. The α-lithio ether intermediates are presumably stabilized by negative hyperconjugation.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: 9-oxabispidines; carbanions; rearrangements; lithiation; bicyclic compounds
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 14:00
Last Modified: 11 Jan 2022 14:00
URI: https://eref.uni-bayreuth.de/id/eprint/68311