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. 2023 Sep 13;13(39):27456-27460.
doi: 10.1039/d3ra04996e. eCollection 2023 Sep 8.

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Veera Babu Gudise  1 , Shaik Anwar  1
Affiliations

Multicomponent reaction (MCR) for constructing bis-spirocyclohexane skeletons using β-nitrostyrene derived MBH acetates, 1,3-indanedione and aldehydes via [1 + 1 + 1 + 3] annulation

Veera Babu Gudise et al. RSC Adv. .

Abstract

An AB2C type four-component quadruple cascade reaction has been established between nitroallylic MBH acetate, 1,3-indanedione and aldehyde for generating bis-spirocyclohexanes. This reaction progressed in an unusual [1 + 1 + 1 + 3] annulation manner via a Knoevenagel/Michael/Michael/Michael sequence, resulting in the generation of three/four chiral centres, and two all-carbon quaternary centres through the formation of 3 new C-C bonds.

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Conflict of interest statement

There are no conflicts of interest.

Figures

Scheme 1
Scheme 1. Construction of substituted bis-spirocyclohexanes using MBH acetates.
Scheme 2
Scheme 2. AB2C type four component quadruple cascade reaction.
Scheme 3
Scheme 3. Gram scale synthesis of bis-spirocyclohexane 8a.
Scheme 4
Scheme 4. Plausible reaction mechanism for the quadruple cascade sequence.
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