Wednesday, June 24, 2009

an interesting paper from Eun Lee

A Carbonyl Ylide Cycloaddition Approach to Platensimycin
Lee, Kim, Jang, Choi and Chung. ACIEE, 2008,















why interesting?
"they knew that a terminal olefin would have the incorrect electronic configuration to lead to the desired product in the [3+2] before attempting the chemistry. However, they did the reaction anyway, and ended out with a cracking yield of the wrong isomer and only a trace of the desired. Playing with the HOMO coefficient by using a vinyl halide in place of the terminal olefin allowed the chemistry to proceed in a tasty 83% yield, with small amounts of the competing products."
from http://totallysynthetic.com/blog/?p=976

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