Issue 32, 2020

One-pot construction of dispirocyclohexanes via K2CO3-mediated desulfonylative Michael–Michael–aldol (2 + 2 + 2) annulation of sulfonyl 2-pyridyl flavanones and methylketones

Abstract

K2CO3-mediated one-pot tandem conversion from sulfonyl 2-pyridyl flavanones to dipyridyl dispirocyclohexanes with contiguous multiple stereogenic centers was accomplished in good yields via an intramolecular desulfonylative ring-contraction of sulfonyl 2-pyridyl flavanones followed by an intermolecular Michael–Michael–aldol (2 + 2 + 2) annulation of the resulting pyridyl aurone intermediate with methyl ketones under facile, open-vessel, inexpensive and environmentally friendly reaction conditions. A plausible mechanism is proposed and discussed herein. This protocol provides a highly effective ring-closure via three carbon–carbon (C–C) bond formation.

Graphical abstract: One-pot construction of dispirocyclohexanes via K2CO3-mediated desulfonylative Michael–Michael–aldol (2 + 2 + 2) annulation of sulfonyl 2-pyridyl flavanones and methylketones

Supplementary files

Article information

Article type
Paper
Submitted
08 Jul 2020
Accepted
24 Jul 2020
First published
24 Jul 2020

Org. Biomol. Chem., 2020,18, 6297-6311

One-pot construction of dispirocyclohexanes via K2CO3-mediated desulfonylative Michael–Michael–aldol (2 + 2 + 2) annulation of sulfonyl 2-pyridyl flavanones and methylketones

M. Chang, K. Chen and H. Chen, Org. Biomol. Chem., 2020, 18, 6297 DOI: 10.1039/D0OB01404D

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