Synthesis of furan-bridged 10-membered rings through [8 + 2]-cycloaddition of dienylfurans and acetylenic esters

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1665-1667

  Zhang, Lei ^a   Wang, Yu ^a   Buckingham, Clare ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BRIDGED COMPOUND; ESTER DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ACETYLENE; CYCLIZATION; ESTERS; FURANS; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; MOLECULAR STRUCTURE;

EID: 17844392059     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050416n     Document Type: Article

References (24)

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15. The [8 + 2]-cycloaddition reaction has been primarily restricted to substrates where carbons 1 and 8 of the tetraene system are rigidly held in close proximity (e.g., methylenecycloheptatrienes). For a review, see: Nair, V.; Anilkumar, G. Synlett 1998, 950-957.
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17. (a) The greatly enhanced reactivity of isobenzofurans (relative to furans) in cycloaddition reactions is well documented. Friedrichsen, W. Adv. Heterocycl. Chem. 1999, 73, 1-96.
18. (b) Ab initio calculations show that ΔE for the [8 + 2]-reaction of butadienylisobenzofuran and acetylene is -51 kcal/mol, while ΔE for [8 + 2]-reaction of butadienylfuran and acetylene is -22 kcal/mol.
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22. A calculation at the 6-31G* level reveals that the regiochemistry of the [8 + 2]-cycloaddition reaction is consistent with that predicted by the MO coefficients of the energy-minimized (s-trans) conformation. There is a higher coefficient at the furan terminus of the tetraene system (0.24) than at the diene terminus (-0.21). This calculation was very dependent on the choice of basis set.
23. The product was assigned as the syn double bond addition product derived through protonation and addition of methoxy from the convex face. This isomer is slightly more stable than the anti isomer; ΔE syn to anti is +0.3 kcal/mol in a simplified analogue of 15 according to ab intio calculations. Trans-bridged furanophanes were not considered due to excessive strain in these systems revealed by MM2 calculations.
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