NXS, Morpholine, and HFIP: The Ideal Combination for Biomimetic Haliranium-Induced Polyene Cyclizations

In contrast to Nature that accomplishes polyene cyclizations seemingly with ease, such transformations are difficult to conduct in the lab. In our program dealing with the development of selective halogenations of alkenes, we now asserted that standard X+ reagents are perfectly suited for the biomim...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-03, Vol.140 (12), p.4344-4353
Main Authors: Arnold, Andreas M, Pöthig, Alexander, Drees, Markus, Gulder, Tanja
Format: Article
Language:English
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Summary:In contrast to Nature that accomplishes polyene cyclizations seemingly with ease, such transformations are difficult to conduct in the lab. In our program dealing with the development of selective halogenations of alkenes, we now asserted that standard X+ reagents are perfectly suited for the biomimetic cation-π cyclization of both electron rich and poor linear polyenes in the presence of the Lewis base morpholine and the Lewis acid HFIP. The method stands out due to its broad substrate scope and practicability together with high chemical yields and excellent selectivities, even for highly challenging chloriranium-induced polyene cyclizations.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b00113