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Mechanistic studies of rearrangements during the ring expansions of cyclopropanated carbohydrates |
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| Authors: | Rhys Batchelor Paul Teesdale-Spittle |
| Institution: | a School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington, New Zealand b School of Biological Sciences, Victoria University of Wellington, Wellington, New Zealand c Department of Chemistry, University of Wyoming, Laramie, Wyoming 82071, USA |
| Abstract: | Deuterium-labeling studies have been performed on the ring expansion of cyclopropanated carbohydrates. From these studies, mechanisms have been proposed for two unusual rearrangements. In addition, a selective deprotection of the 1,3-di-tert-butylsilyl ether protecting group at the secondary position versus the primary position has been observed. This is a high yielding transformation with the potential for general synthetic utility. |
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