Organic Chemistry Portal
Reactions > Organic Synthesis Search

C-O Bond Formation, C-C Bond Formation > Oxygen-containing molecules >

Synthesis of 1,3-diols

Name Reactions

Prins Reaction

Recent Literature

C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderate diastereoselectivity and enantioselectivity. The best results were achieved using Hashimoto's Rh2((S)-PTTL)4 catalyst.
H. M. L. Davies, S. J. Hedley, B. R. Bohall, J. Org. Chem., 2005, 70, 10737-10742.

A catalytic, direct asymmetric cross-aldol reaction of two different aldehydes in the presence of water is catalyzed by a novel combined proline-surfactant organocatalyst. Neither an organic cosolvent nor additional acid is necessary.
Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. Int. Ed., 2006, 45, 5527-5529.

Direct Catalytic Asymmetric Aldol-Tishchenko Reaction
V. Gnanadesikan, Y. Horiuchi, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 7782-7783.

Ketones, dienes, and B2(pin)2 undergo a stereoselective multicomponent coupling reaction in the presence of catalytic amounts of Ni(cod)2 and P(t-Bu)3. A subsequent oxidation furnishes 1,3-diols as the major reaction product.
H. Y. Cho, Z. Yu, J. P. Morken, Org. Lett., 2011, 13, 5267-5269.


A novel microwave-assisted, operationally simple, tandem bis-aldol reaction of ketone with paraformaldehyde catalyzed by polystyrenesulfonic acid in aqueous medium delivers 1,3-dioxanes in high yield.
V. Polshettiwar, R. S. Varma, J. Org. Chem., 2007, 72, 7420-7422.

An organocatalytic β-hydroxylation of α,β-unsaturated aldehydes with commercially available (E)-benzaldehyde oxime gives the corresponding chiral carbonyl β-oxime ethers in high yields and with excellent enantioselectivities. The chiral carbonyl β-oxime ethers can be reduced to the corresponding 1,3-diols in high yields.
S. Bertelsen, P. DinÚr, R. L. Johansen, K. A. J°rgensen, J. Am. Chem. Soc., 2007, 129, 1536-1537.