Aldol

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General aldol structure showing the α and 𝛽 positions of carbons relative to the carbonyl. When R3 is -H, it is an aldol, when R3 is a carbon, it is a ketol.

In

3-hydroxybutanal.[1][2]

Aldols are the product of a carbon-carbon bond-formation reaction, giving them wide applicability as a pre-cursor for a variety of other compounds.

Synthesis and reactions

chiral centers
: A: OH is 4R, R-group is 3R B: OH is 4S, R-group is 3S C: OH is 4R, R-group is 3S D: OH is 4S, R-group is 3R

Aldols are usually synthesized from an

asymmetric synthesis
.

Aldols may also undergo a condensation reaction in which the hydroxy group is replaced by a pi bond. The final structure is a reactive α,β-unsaturated carbonyl compound, which can also used in a variety of other reactions:

RC(O)CH2CH(OH)R' → RC(O)CH=CHR' + H2O

Applications

Aldols synthesized from two aldehydes are usually unstable, often producing secondary compounds such as diols, unsaturated aldehydes, or alcohols.[1] Hydroxypivaldehyde is a rare example of a distillable aldol.[3] The aldol 3-hydroxybutanal is a precursor to quinaldine, which is a precursor to the dye quinoline Yellow SS.[1]

Aldols are also used as intermediates in the synthesis of polyketide natural products and drugs such as Oseltamivir and Epothilone.[4][5][6][7]

See also

References

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