An Efficient and Enantioselective Approach to 2,5-Disubstituted ­Dihydropyrones

This review is focused on the enantioselective synthesis of 3,4-dihydropyran derivatives, whose importance as chiral building blocks in the synthesis of bioactive molecules and natural products is well established. The review analyzes the different synthetic strategies by grouping them as a function of the atom numbers of the reagents involved. Starting from the classical [4 + 2] and [2 + 4] approaches, the [3 + 3], [5 + 1], and [6] strategies have been sequentially analyzed, and for each of them, the asymmetry induced by both chiral metal complexes and different kinds of organocatalysts has been examined. More than 400 papers have been reviewed, whose results have been described in the highest synthetic manner, in the attempt to emphasize the mechanism of the chirality transfer from the chiral messengers to the reaction products. This analysis allows the great flexibility of the diverse catalytic systems, the complementary of the results obtained from the different reaction pathways, and the very high level of control of the achievable molecular complexity to be evidenced.

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Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives

Desimoni

2018

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Asymmetric synthesis of 2,6-substituted dihydropyrone catalyzed by 3-monosubstituted and 3,3′-bisubstituted BINOL titanium complexes

Zhang

Zhao

et al. 2008

Chemical Papers

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Asymmetric hetero-Diels-Alder (HDA) reactions of aromatic aldehydes with Danishefsky’s diene derivative were carried out smoothly in the presence of the Ti(IV)-(R)-BINOL (1:1.2) complex to give the corresponding chiral 2,6-disubstituted dihydropyrones under mild conditions. The readily accessible I-Ti(OCH(CH3)2)4 (1.2:1) complex was found to be an effective catalyst for this reaction. Aromatic aldehydes afforded the corresponding products in moderate yields (up to 72 %) with good enantioselectivities (up to 80 % ee). Aromatic aldehydes in presence of the TiCl4-NaOCH3-II (1:4.2:1.2) complex gave the products in higher yields (up to 73 %) with better enantioseletivities (up to 84 % ee).

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An Efficient and Enantioselective Approach to 2,5-Disubstituted Dihydropyrones

Cited by 2 publications

References 1 publication

Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives

Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives

Asymmetric synthesis of 2,6-substituted dihydropyrone catalyzed by 3-monosubstituted and 3,3′-bisubstituted BINOL titanium complexes

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An Efficient and Enantioselective Approach to 2,5-Disubstituted ­Dihydropyrones

Cited by 2 publications

References 1 publication

Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives

Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives

Asymmetric synthesis of 2,6-substituted dihydropyrone catalyzed by 3-monosubstituted and 3,3′-bisubstituted BINOL titanium complexes

Contact Info

Product

Resources

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An Efficient and Enantioselective Approach to 2,5-Disubstituted Dihydropyrones