Organic Letters
Letter
discussions. Li Li (MIT) is acknowledged for HRMS data,
which were obtained on an instrument purchased with the
assistance of NSF Grant CHE-0234877. NMR spectroscopy
was carried out on instruments purchased in part with funds
provided by the NSF (CHE-9808061 and CHE-8915028).
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(13) For a full evaluation of Lewis acid catalysts and other reaction
conditions, see the Supporting Information for details.
(14) We cannot rule out the possibility that oxonium 7 undergoes
chloride attack to generate the corresponding chloromethyl ether
intermediate; however, since gem-dimethyl groups are tolerated in the
2-position, it is more likely that the mechanism proceeds via
oxocarbenium intermediate 8.
(15) For full details, see the Supporting Information.
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(18) Enantioselectivity was determined by chiral HPLC of an
intermediate that was further functionalized. See the Supporting
Information for details.
D
Org. Lett. XXXX, XXX, XXX−XXX