Synlett 2023; 34(20): 2465-2470
DOI: 10.1055/a-2102-7866
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto

Organocatalyzed Regioselective α,γ-Difunctionalization of Deconjugated Butenolides: Synthesis of Butyrolactone–Butyrolactam Hybrid Molecules

Swati Lekha Mondal
,
Koushik Patra
,
Rahul Yadav
,
Mahiuddin Baidya

We gratefully acknowledge financial support from Science and Engineering Research Board (SERB), India (EMR/2014/000225) and Indian Institute of Technology Madras (IIT) Madras (IOE project). S.L.M. acknowledges a fellowship from the Council of Scientific and Industrial Research, India and K.P. acknowledges a Prime Minister’s Research Fellows (PMRF) fellowship.


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On the occasion of Prof. H. Yamamoto’s 80th birthday

Abstract

A highly regioselective α,γ-difunctionalization of deconjugated butenolides that allows access to hybrid molecular frameworks composed of unsaturated butyrolactone and butyrolactam motifs is reported. The reaction is catalyzed by inexpensive quinidine, and products are isolated in high yields as a single diastereomer. The γ-selective monofunctionalization was also accomplished through substrate modification.

Supporting Information



Publication History

Received: 25 April 2023

Accepted after revision: 30 May 2023

Accepted Manuscript online:
30 May 2023

Article published online:
14 July 2023

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