δ-Acetoxy Allenoate as a 5C-Synthon in Domino-Annulation with Sulfamidate Imines: Ready Access to Coumarins

A DMAP-catalyzed sequential benzannulationand lactonization strategyin which & delta;-acetoxy allenoate functions as a 5C-synthon in its reaction with cyclic sulfamidate imines is reported. Thisplatform delivers & pi;-extended coumarin frameworks under metal-freeconditions via allylic elimin...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 88; no. 17; pp. 12432 - 12444
Main Authors: Chauhan, Sachin, Kumar, A. Sanjeeva, Swamy, K. C. Kumara
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 01.09.2023
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
DELTA-ACETOXY ALLENOATES
PHOSPHINE-CATALYZED CYCLOADDITION
REACTIVITY
CASCADE
AMINE
ALLENES
ISSN:0022-3263, 1520-6904, 1520-6904
Online Access:Get more information
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Summary:A DMAP-catalyzed sequential benzannulationand lactonization strategyin which & delta;-acetoxy allenoate functions as a 5C-synthon in its reaction with cyclic sulfamidate imines is reported. Thisplatform delivers & pi;-extended coumarin frameworks under metal-freeconditions via allylic elimination followed by Mannich coupling, protonshifts, C-N bond cleavage, and lactonization as key steps.The driving force for this domino reaction is the formation of thediene-ammonium intermediate and O-S bond cleavage. ESI-HRMShas been useful in gaining insights into the reaction pathway.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01183