2007
DOI: 10.1002/adsc.200600473
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Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Abstract: Enantiomerically pure 1,5-hexadiene-3,4-diol, derived from d-mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring sizeselective ring-closing metathesis reaction of a triene. Most likely, a catalyst-directing effect of an allylic hydroxy group is responsible for the selectivity.

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Cited by 45 publications
(40 citation statements)
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“…Formation of benzyl ether 6 has previously been described in the literature. [47,49] Vanadiumcatalysed epoxidation of 6 was investigated in different context by us. [50] The reaction yields epoxide 7 [50] in good yield and perfect regioselectivity within short periods of time.…”
Section: Resultsmentioning
confidence: 99%
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“…Formation of benzyl ether 6 has previously been described in the literature. [47,49] Vanadiumcatalysed epoxidation of 6 was investigated in different context by us. [50] The reaction yields epoxide 7 [50] in good yield and perfect regioselectivity within short periods of time.…”
Section: Resultsmentioning
confidence: 99%
“…[ [45][46][47] is conveniently available from -mannitol in few steps. Interestingly, the (S,S)-enantiomer of this compound is also available in few steps from -tartrate.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Diol 1 has been used in target molecule synthesis, [7][8][9][10][11][12][13][14][15][16][17][18][19] as a chiral diene ligand in asymmetric catalysis, [20] and as a probe for catalyst directing effects by hydroxy groups in ring-closing metathesis (RCM) reactions. [6,21,22] The enantiomer, ent-1, has been synthesized by Blechert and co-workers from d-(-)-tartrate and employed in the total synthesis of phomopsolide by using cross metathesis and a subsequent RCM step. [23] In this and many other cases, desymmetrization of 1 or ent-1 is achieved by monofunctionalization of one OH group, often with a bulky protecting group.…”
Section: Introductionmentioning
confidence: 99%
“…[1] C 2 -Symmetric building blocks are particularly useful because they have homotopic functional groups and can be desymmetrized by selective monofunctionalization. [2] Accordingly, (3R,4R)-hexa-1,5-diene-3,4-diol (1), which is available from d-mannitol in a few steps, [3][4][5][6] is a very useful ex-chiral-pool starting material. Diol 1 has been used in target molecule synthesis, [7][8][9][10][11][12][13][14][15][16][17][18][19] as a chiral diene ligand in asymmetric catalysis, [20] and as a probe for catalyst directing effects by hydroxy groups in ring-closing metathesis (RCM) reactions.…”
Section: Introductionmentioning
confidence: 99%