Comments on: Mukaiyama Thioester Synthesis http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/ News, Analysis, and Commentary for the World of Chemistry & Chemical Research Fri, 24 May 2013 16:42:38 +0000 hourly 1 http://wordpress.org/?v=3.5.1 By: milkshake http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8883 milkshake Wed, 28 Sep 2011 22:31:49 +0000 http://blog.chembark.com/?p=1908#comment-8883 there is a fairly nice Staudinger ligation version that takes advantage of Mukaiyama: RCO2H + ‘RN3 + PPh3(excess) = RCONHR’ + N2 + Ph3PO. The catalyst for this reaction is Pyr-Se-Se-Pyr that generates a somewhat more reactive RCOSePyr in situ, which then acylates the iminophosphorane. The reaction still requires strictly anhydrous conditions but it can be run at room temp overnight. (This could be actually quite useful in biopolymer and peptide chemistry.)

]]> By: darksyde http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8874 darksyde Tue, 27 Sep 2011 17:33:49 +0000 http://blog.chembark.com/?p=1908#comment-8874 One of the huge reasons why I hate Big Bang Theory is that it’s made the fucking “ferrous wheel” tee shirts really popular, and now a google search of “ferrous wheel” just puts up a bunch of bullshit. Thanks for shitting in the pool, C&EN.

]]> By: Paul http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8854 Paul Mon, 26 Sep 2011 14:06:53 +0000 http://blog.chembark.com/?p=1908#comment-8854 @See Arr Oh: How dare you impugn the fragrant bouquet of thiols? How dare you?

]]> By: Curious Wavefunction http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8853 Curious Wavefunction Mon, 26 Sep 2011 12:21:06 +0000 http://blog.chembark.com/?p=1908#comment-8853 Jaw-dropping. Off I go to prove that a 30 step natural product synthesis can be performed using only the Mukaiyama Thioester Synthesis and no other reaction, at room temperature in a kitchen sink with only water as a solvent and traces of a snickerdoodle catalyst. Bionic Brothers here I come.

]]> By: Macdrifter » Blog Archive » Reactions (not what you think)[Link] http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8852 Macdrifter » Blog Archive » Reactions (not what you think)[Link] Mon, 26 Sep 2011 11:43:14 +0000 http://blog.chembark.com/?p=1908#comment-8852 [...] This kind of stuff is why I fell in love with Organic Chemistry and spent half my life in school to learn it. [...]

]]> By: See Arr Oh http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8851 See Arr Oh Mon, 26 Sep 2011 11:41:09 +0000 http://blog.chembark.com/?p=1908#comment-8851 “The reaction is clearly the greatest in history.”

Wow, I mean, how far off was I? Once I saw the inherent beauty in the super-stoichiometric phosphine oxides and stinky thiol byproducts, I said to myself “I am going to go delete my post, and put up a page full of links to Paul’s post.”

I’d advise all other participants to do the same. No sense in taking home 4th prize.

]]> By: Ricola http://blog.chembark.com/2011/09/25/mukaiyama-thioester-synthesis/#comment-8848 Ricola Mon, 26 Sep 2011 09:17:44 +0000 http://blog.chembark.com/?p=1908#comment-8848 Hahah a lovely (re)post. If I’m ever going to run this reaction, I too will describe it as the ‘Mukaiyama Thioester Synthesis’ in the manuscript. :-P

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