Efficient Synthesis of 3-Alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones by a Stork–Danheiser Sequence from Vinylogous Esters and Terminal Alkynes

Amarchand Parida; Mohd. Sharique; Badrinath N. Kakde; Santanu Ghosh; Alakesh Bisai

doi:10.1055/s-0034-1380451

Synthesis, Table of Contents

Synthesis 2015; 47(19): 2965-2970
DOI: 10.1055/s-0034-1380451

special topic

Efficient Synthesis of 3-Alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones by a Stork–Danheiser Sequence from Vinylogous Esters and Terminal Alkynes

Authors

Amarchand Parida

Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462066, India Email: alakesh@iiserb.ac.in
Mohd. Sharique

Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462066, India Email: alakesh@iiserb.ac.in
Badrinath N. Kakde

Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462066, India Email: alakesh@iiserb.ac.in
Santanu Ghosh

Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462066, India Email: alakesh@iiserb.ac.in
Alakesh Bisai*

Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, MP 462066, India Email: alakesh@iiserb.ac.in

Abstract

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Abstract

An efficient Stork–Danheiser sequence has been developed for the preparation of a variety of 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones in good to excellent yields from the corresponding 4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-ones and terminal alkynes. Several of the 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-one products were catalytically cyclized to give the corresponding 3-aryl-1,5,6,7-tetrahydro-8H-isochromen-8-ones.

Key words

alkynylations - Stork–Danheiser sequences - vinylogous esters - alkynes - cyclizations - chromenones

Full Text

References

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Supplementary Material

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