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Synthesis of Chiral γ-lactones by One-Pot Sequential Enantioselective Organocatalytic Michael Addition of Boronic Acids and Diastereoselective Intramolecular Passerini Reaction

Synthesis of Chiral γ-lactones by One-Pot Sequential Enantioselective Organocatalytic Michael Addition of Boronic Acids and Diastereoselective Intramolecular Passerini Reaction

Maxence Bos, Emmanuel Riguet

J Org Chem. 2014 Nov 21;79(22):10881-9.

PMID: 25365780

Abstract:

The synthesis of α,γ-substituted chiral γ-lactones was quickly achieved in a one pot sequential process. The procedure involves an enantioselective organocatalysed transfer of boronic acid to 5-hydroxyfuran-2(5H)-one, followed by an intramolecular diastereoselective Passerini-type reaction. The methodology was developed and optimized with N-Boc-indole-2-boronic acid giving access to α-indole-γ-substituted lactones in high yields and good diastereoisomeric and enantiomeric ratios. By applying the process to other boronic acids, the synthesis of structurally diversified α,γ-substituted chiral lactones was also achieved in good yields albeit with lower enantioselectivities.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP213318446	N-Boc-indole-2-boronic acid		213318-44-6	Price

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