C O M M U N I C A T I O N S
Table 1. Synthesis of Alkynyl Epoxides
Supporting Information Available: Preparative procedures, ana-
lytical and spectral data. This material is available free of charge via
References
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(7) Reaction of 1b with phenylalkynyl chloride under standard reaction
conditions led to R-alkynylated product, exclusively.
(8) Employment of primary and secondary enolizable ketones, as well as
nonaromatic ketones, led to complex mixtures of products.
(9) Cyclizations of 1k,l with 2a produced unseparable mixtures of diastereomers
5ka, 5la. See Supporting Information for details.
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a Isolated yields. b Iodoalkynylbenzene was used. c KHMDS was used
as a base. d The reaction was performed at 0 °C. e Yield of the
desilylated product. See Supporting Information for details.
(12) The involvement of free acetylide species in this transformation was
additionally supported by the results of the following cross-over experiment.
See Supporting Information for details.
species in the same cascade transformation. This allowed for
development of a novel and efficient one-step synthesis of alky-
nylepoxides, highly valuable organic synthons,10 from easily
available enolizable ketones.
Acknowledgment. The support of the National Science Foun-
dation (Grant CHE-0710749) is gratefully acknowledged.
JA806178R
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