DABCO-catalysed highly diastereoselective synthesis of 1,3-indandione containing fully saturated spirocyclopentanes involving 2-(2′-ketoalkyl)-1,3-indandiones and nitrostyrenes

Gitanjali Mishra; Missa Saril Bobonga; Kamrul Islam; Arundhuti Chakraborty; Barla Thirupathi

doi:10.1039/d5ra04224k

January 1, 2025RSC AdvancesOpen Access

DABCO-catalysed highly diastereoselective synthesis of 1,3-indandione containing fully saturated spirocyclopentanes involving 2-(2′-ketoalkyl)-1,3-indandiones and nitrostyrenes

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Key Points

The synthesis yields highly functionalized 1,3-indandiones with three consecutive chiral centres and a spirocyclic centre.
Products are formed with significant diastereoselectivity when using DABCO as a catalyst in the reaction with nitrostyrenes.
The process involves a reaction between nitrostyrenes and 2-(2'-ketoalkyl)-1,3-indandiones, emphasizing the role of DABCO.
This method may facilitate more efficient syntheses of complex molecular architectures in organic chemistry.

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Implication

Study demonstrates DABCO-catalysed diastereoselective synthesis of 1,3-indandiones with nitrostyrenes, highlighting the formation of multiple chiral centres.

Abstract

Highly functionalized 1,3-indandione containing spirocyclopentanes has been synthesized by reacting nitrostyrenes with 2-(2'-ketoalkyl)-1,3-indandiones using a catalytic amount of DABCO. The resultant products possess three consecutive chiral centres in addition to a spirocyclic centre and are obtained in a highly diastereoselective manner using a catalytic amount of the organic base, DABCO.

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Mishra et al. (2025) studied this question.

synapsesocial.com/papers/68bb3d5b2b87ece8dc956400 https://doi.org/10.1039/d5ra04224k

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DABCO-catalysed highly diastereoselective synthesis of 1,3-indandione containing fully saturated spirocyclopentanes involving 2-(2′-ketoalkyl)-1,3-indandiones and nitrostyrenes

Key Points

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Implication

Abstract

Discussion

Cite This Study

DABCO-catalysed highly diastereoselective synthesis of 1,3-indandione containing fully saturated spirocyclopentanes involving 2-(2′-ketoalkyl)-1,3-indandiones and nitrostyrenes

Key Points

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Implication

Abstract

Discussion

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