Beilstein J. Org. Chem.2010,6, 1219–1228, doi:10.3762/bjoc.6.140
chalcogen effect in protein modifications via olefin metathesis and the associated principles of cross-metathesis (CM) partner selection for reliable and efficient reaction on proteins are also highlighted.
The effect of allylic hydroxy groups in olefin metathesis
The activating effect of allylic hydroxy
favorable than the sulfur in allyl sulfides. While, as a single example, Kotetsu and co-workers have synthesized selenium-containing bicyclic β-lactams via RCM of an allyl selenide derivative, enhanced reactivity was unnoticed [39]. With a better understanding of the allylic chalcogen effect, olefin
chalcogen effect has affected the way chemists use metathesis in synthesis and chemical biology. Complex molecules and metathesis partners can be joined efficiently with the aid of the natural affinity of ruthenium for allyl chalcogens. In this review, we have highlighted various applications of olefin
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Graphical Abstract
Scheme 1:
a) Variation of olefin metathesis: CM = cross-metathesis; RCM = ring-closing metathesis; ROM = ring...
Beilstein J. Org. Chem.2010,6, 1002–1014, doi:10.3762/bjoc.6.113
ultimately lead to orbital overlap in one dimension, albeit through a combination of chalcogen–chalcogen and π–π contacts.
The UV–visible electronic absorption spectra of compounds 3, 25, 27 and 28 were recorded in CH2Cl2 solution and are shown in Figure 6. The spectra of thione 3 and ethylenedithio-bridged