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. 2011 May 20;13(10):2686-9.
doi: 10.1021/ol200782d. Epub 2011 Apr 19.

Regioselective hydroformylation of allylic alcohols

Thomas E Lightburn  1 , Omar A De Paolis, Ka H Cheng, Kian L Tan
Affiliations

Regioselective hydroformylation of allylic alcohols

Thomas E Lightburn et al. Org Lett. .

Abstract

A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.

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Figures

Scheme 1
Scheme 1
Hydroformylation of Trisubstituted Olefins
Scheme 2
Scheme 2
Acetal protection of hydroformylation products
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