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The Dess‐Martin periodinane: 1,1,1‐triacetoxy‐1,1‐dihydro‐1,2‐benziodoxol‐3(1H)‐one intermediate: 1‐Hydroxy‐1,2‐benziodoxol‐3(1H)‐one 1‐oxide (1) product: 1,1,1‐Triacetoxy‐1,1‐dihydro‐1,2‐benziodoxol‐3(1H)‐one (2)

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The direct enantioselective hydroxymethylation of aldehydes utilizing alpha,alpha-diphenylprolinol trimethylsilyl ether as an organocatalyst is described. The intermediate alpha-substituted beta-hydroxyaldehydes were not isolated but converted to the more readily isolable derivatives. For example, the derived hydroxy acids were isolated in up to 94% yield with excellent enantioselectivity.

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