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Beilstein J. Org. Chem. 2010, 6, 1219–1228, doi:10.3762/bjoc.6.140
Graphical Abstract
Scheme 1: a) Variation of olefin metathesis: CM = cross-metathesis; RCM = ring-closing metathesis; ROM = ring...
Figure 1: Allylic hydroxy activation in RCM [19].
Figure 2: Possible complexes generated through preassociation of allylic alcohol with ruthenium.
Scheme 2: The influence of different OR groups on ring size-selectivity [21].
Scheme 3: Synthesis of palmerolide A precursors by Nicolaou et al. illustrates enhancement by an allylic hydr...
Scheme 4: a) Acceleration of ring-closing enyne metathesis by the allylic hydroxy group [23]. b) Proposed mode of...
Scheme 5: a) Effect of the hydroxy group on the rate and steroselectivity of ROCM [24]. b) Proposed H-bonded ruth...
Scheme 6: Plausible explanation for chemoselective CM of diene 16 [25].
Scheme 7: a) Efficient cross-metathesis of S-allylcysteine [17]. b) Comparison of relative reactivity between all...
Scheme 8: a) Macrocycle synthesis by carbonyl-relayed RCM. b) Putative complex in carbonyl-relayed RCM [33].
Scheme 9: a) Sulfur assisted cross-metathesis [17]. b) Putative unproductive chelates for larger ring sizes gener...
Scheme 10: Functionalization of Mukaiyama aldol product by CM in aqueous media [37].
Scheme 11: Comparison of reactivity between allyl sulfides and allyl selenides in aqueous cross-metathesis [38].
Scheme 12: Ring-closing metathesis on a protein [18].
Scheme 13: Expanded substrate scope of cross-metathesis on proteins [38].