A diastereoselective tandem RCM approach to spiropiperidines

Tetrahedron

Volumn 60, Issue 40, 2004, Pages 8869-8880

  Wybrow, Robert A J ^a   Edwards, Andrew S ^a   Stevenson, Neil G ^a   Adams, Harry ^a   Johnstone, Craig ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Metathesis reactions; Tandem RCM approach; Tetraene substrates

Indexed keywords

CARBENE; PIPERIDINE DERIVATIVE; RUTHENIUM; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; DIASTEREOISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 4444301978     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.025     Document Type: Article

References (35)

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27. 4 led to over oxidation and poor selectivity for dihydroxylation of the more remote alkene.
28. We were unable to unambiguously establish the stereochemistry of the major piperidine 25. However, we have carried out the conversion of 25 to 24 using both Ru-catalysts I and II under a variety of conditions and have found the diastereomeric ratio of starting 25 to be conserved in the spirodiene product 24. We therefore conclude that the major diastereoisomer of 25 produced from the reaction in Scheme 7 to be that shown below: 25
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34. Crystallographic data (excluding structure factors) for structure 27 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 237218. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Rd, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
35. 2O, RT, 18 h) did not lead to dihydroxylation of either olefin and starting material was recovered.