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Regioselective hydroformylation of allylic alcohols

Organic Letters 13(10): 2686-2689

Regioselective hydroformylation of allylic alcohols

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.

Accession: 055445677

PMID: 21504208

DOI: 10.1021/ol200782d

Related references

Liao, J.; Guo, W.; Zhang, Z.; Tang, X.; Wu, W.; Jiang, H., 2016: Metal-Free Catalyzed Regioselective Allylic Trifluoromethanesulfonylation of Aromatic Allylic Alcohols with Sodium Trifluoromethanesulfinate. An efficient procedure for the preparation of allylic trifluoromethanesulfones with high regioselectivity from aromatic allylic alcohols/esters and NaSO2CF3 under transition-metal-free conditions is described. A wide range of functional groups wer...

Discordia R.P.; Murphy C.K.; Dittmer D.C., 1990: Telluride mediated stereospecific conversion of racemic e allylic alcohols to homochiral z allylic alcohols transposition of primary and secondary allylic alcohols via glycidol derivatives. Tetrahedron Letters 31(39): 5603-5606

Nozaki, K.; Li, W.-Ge; Horiuchi, T.; Takaya, H., 1997: Asymmetric hydroformylation of allylic alcohols catalyzed by Rh(I)-(R,S)-BINAPHOS. Chiral lactones 4a-e were synthesized by the asymmetric hydroformylation of allylic alcohols 1a-e and 5 catalyzed by a rhodium(I) complex of a chiral phosphine-phosphite, (R,S)- BINAPHOS. followed by the silver(I) oxidation.

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Wang, J.; Huang, W.; Zhang, Z.; Xiang, X.; Liu, R.; Zhou, X., 2009: FeCl(3).6H(2)O catalyzed disproportionation of allylic alcohols and selective allylic reduction of allylic alcohols and their derivatives with benzyl alcohol. Iron chloride has been found to be an efficient catalyst for the disproportionation of allylic alcohols, which provides a convenient method for selective transformation of allylic alcohols to alkenes and alpha,beta-unsaturated ketones. Furthermore...

Breit, B.; Demel, P.; Gebert, A., 2004: Directed regio- and stereoselective hydroformylation of mono- and 1,3-disubstituted allylic alcohols: a catalytic approach to the anti-aldol-retron. Regioselective and diastereoselective hydroformylation of mono- and 1,3-disubstituted allylic alcohol o-DPPB esters is described. The products represent synthetically important anti-aldol retrons.

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