Re: ORGLIST: borohydride reduction

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From: support$##$cussyn.com
Date: Tue Nov 30 2004 - 15:56:14 EST


Mats,

If you have other olefins in the molecule, one possibility is
to convert to the saturated ester and reduce with NaBH4.
Using a lewis base catalyzed formation of the cyanohydrin and
consequent decomp with alcohol to give the sat. ester.

By reacting your cmpd (in MeCN) with 5 mol% DBU and
TMS-cyanide at 28C for ~5h or until complete consumption of
the aldehyde, then add MeOH w addn stirring you should end up
with conversion to the SATURATED Ester which can be easily
reduced. I would think that this strategy would work on your
posted 2E,6Z-decadienal to the alcohol 6Z-decenol synthesis
problem.

Check out Tetrahedron Letters 2002,43,(5645-5647) for the
specifics on this transformation.

Good Luck,

Brad

Brad Droessler
Senior Scientist-Chemist
Manager of Scientific Operations
Custom Synthesis Services
support$##$cussyn.com
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