Journal
TETRAHEDRON LETTERS
Volume 52, Issue 49, Pages 6541-6544Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.09.124
Keywords
Carbocyclization; Titanium chloride; Methylenecyclopropanes; Propargylic esters; Ring enlargement
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Funding
- Shanghai Municipal Committee of Science and Technology [08dj1400100-2]
- National Basic Research Program of China (973) [2009CB825300]
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China [21072206, 20472096, 20872162, 20672127, 20821002, 20732008]
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Titanium(IV) chloride-mediated intramolecular ring enlargement of methylenecyclopropanes with propargylic esters has been described in this context, affording the corresponding chlorinated bicyclo[4.2.0]oct-5-ene derivatives in moderate to good yields under mild conditions. The E- and Z-methylenecyclopropanes could all be converted to the corresponding bicyclo[4.2.0]oct-5-enes with moderate to high diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
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