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Topic: TIPS-ether: compatability & guiding group for Sharpless-AD?  (Read 1545 times)

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Offline yesway

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TIPS-ether: compatability & guiding group for Sharpless-AD?
« on: October 11, 2012, 09:50:55 AM »
Hi,

theoretical question: for asymmetric dihydroxylation of E-Pent-2-ene-1,4-diol , my plan was to introduce necessary steric bulk at the primary alcohol position with TIPSCl. I wonder if this would work with the AD reaction in terms of compatability & and the TIPS ether as a guiding group.
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Offline discodermolide

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Re: TIPS-ether: compatability & guiding group for Sharpless-AD?
« Reply #1 on: October 11, 2012, 09:55:47 AM »
I don't see why this would not work. Only one way to find out. But the AD is pretty good anyway, at least that's been my experience with it.
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Offline yesway

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Re: TIPS-ether: compatability & guiding group for Sharpless-AD?
« Reply #2 on: October 11, 2012, 10:03:24 AM »
Ok, thanks - I had my doubts because so many working examples from literature/textbooks were based on styrene patterns!
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