ORGLIST:Full reduction of a,b-unsaturated aldehydes

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From: Mats Hamberg (matham$##$mbox.ki.se)
Date: Tue May 11 2004 - 02:18:57 EDT

Greetings,
In a synthesis sequence, I need to convert 2E,6Z-decadienal to the alcohol 6Z-decenol, i.e. to perform a full reduction of the a,b-unsaturated aldehyde. I have tried NaBH4 in methanol, aq. methanol and aq. pyridine as well as LiAlH4 in ether or THF. These treatments afford 2E,6Z-decadienol. NaBH4 in the presence of CoCl2 affords decanal (saturation of both double bonds).

Which metal hydride / condition should be used to effect the unsaturated aldehyde -> saturated alcohol conversion in good yield?

Any help is appreciated.

Best regards,

Mats Hamberg
MBB, Karolinska Institutet
Stockholm, Sweden
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