The high stereoselectivity of the tandem sequence Diels-Alder reaction : Ireland-Claisen rearrangement starting from substituted O-(E)-buta-1,3-dienyl ketene acetals and cyclic dienophiles

A new tandem reaction leads to bicyclic cyclohexene derivatives with complete control of the relative configuration of the four chiral centers formed. The high diastereoselectivity is the consequence of an endo-selective Diels-Alder reaction followed by an Ireland-Claisen rearrangement that proceeds via a boat-like transition state. © Georg Thieme Verlag Stuttgart.


Published in:
Synthesis, 15, 15, 2379-2387
Year:
2007
ISSN:
00397881
Note:
422
Other identifiers:
Scopus: 2-s2.0-34547749424
Laboratories:




 Record created 2009-05-12, last modified 2018-09-13


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