Striking contrasts in stereoselectivities of spiro-claisen rearrangements of pyranosides versus carbocycles. |
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| Authors: | Bert Fraser-Reid Deen B. Tulshian Ray Tsang Derek Lowe Vernon G.S. Box |
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| Affiliation: | Paul M. Gross Chemical Laboratory Duke University, Durham, NC 27706 U.S.A.;Department of Chemistry City University of New York, City College New York, NY 10031 U.S.A. |
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| Abstract: | Structurally equivalent derivatives of pyranosides and cyclohexanes undergo the spiro-Claisen rearrangement with different stereochemical results. A rationalization for the course observed with the pyranosides is suggested, which invokes interaction of the oxygen lone pair with a (developing) electron deficient centre at the spiro carbon. |
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