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Search for "allyl substituent effect" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

The allylic chalcogen effect in olefin metathesis

Yuya A. Lin and
Benjamin G. Davis

Beilstein J. Org. Chem. 2010, 6, 1219–1228, doi:10.3762/bjoc.6.140

. Keywords: allyl substituent effect; allyl sulfides; aqueous chemistry; olefin metathesis; protein modifications; Review Olefin metathesis is one of the most useful chemical transformations for forming carbon–carbon bonds in organic synthesis (Scheme 1) [1][2][3][4]. The broad utility of olefin metathesis

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Graphical Abstract

Scheme 1: a) Variation of olefin metathesis: CM = cross-metathesis; RCM = ring-closing metathesis; ROM = ring...

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Figure 1: Allylic hydroxy activation in RCM [19].

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Figure 2: Possible complexes generated through preassociation of allylic alcohol with ruthenium.

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Scheme 2: The influence of different OR groups on ring size-selectivity [21].

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Scheme 3: Synthesis of palmerolide A precursors by Nicolaou et al. illustrates enhancement by an allylic hydr...

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Scheme 4: a) Acceleration of ring-closing enyne metathesis by the allylic hydroxy group [23]. b) Proposed mode of...

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Scheme 5: a) Effect of the hydroxy group on the rate and steroselectivity of ROCM [24]. b) Proposed H-bonded ruth...

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Scheme 6: Plausible explanation for chemoselective CM of diene 16 [25].

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Scheme 7: a) Efficient cross-metathesis of S-allylcysteine [17]. b) Comparison of relative reactivity between all...

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Scheme 8: a) Macrocycle synthesis by carbonyl-relayed RCM. b) Putative complex in carbonyl-relayed RCM [33].

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Scheme 9: a) Sulfur assisted cross-metathesis [17]. b) Putative unproductive chelates for larger ring sizes gener...

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Scheme 10: Functionalization of Mukaiyama aldol product by CM in aqueous media [37].

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Scheme 11: Comparison of reactivity between allyl sulfides and allyl selenides in aqueous cross-metathesis [38].

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Scheme 12: Ring-closing metathesis on a protein [18].

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Scheme 13: Expanded substrate scope of cross-metathesis on proteins [38].

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Review

Published 23 Dec 2010

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