Magic ring catenation by olefin metathesis

Organic Letters

Volumn 7, Issue 11, 2005, Pages 2129-2132

  Guidry, Erin N ^a   Cantrill, Stuart J ^b   Stoddart, J Fraser ^b   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMMONIA; CATENANE; CROWN ETHER; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 20444474543     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050463f     Document Type: Article

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56. 6, which is formed during the ring-closing metathesis (RCM) macrocyclization of the diolefin 8. Olefin isomerization prior to the RCM reaction affords a macrocycle with one methylene deletion, resulting in a 26-membered ring, rather than the expected 27-membered one.
57. 6) was obtained following acylation of this compound under basic conditions. The acylated product, in which the mutual recognition expressed between the two mechanically interlocked rings has been removed, was proven to be a single species that had not fallen apart, as evidenced by both NMR spectroscopy and ESI mass spectrometry; see Supporting Information.
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