Mn-catalyzed radical initiated domino transformation of alkynylated cyclohexadienones with TMSN3 and O2 to bicyclic azido alcohols

Pranesh Pal; Prathama S. Mainkar; Kiranmai Nayani; Srivari Chandrasekhar

doi:10.1039/D0CC00102C

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Mn-catalyzed radical initiated domino transformation of alkynylated cyclohexadienones with TMSN₃ and O₂ to bicyclic azido alcohols†

Pranesh Pal,^ab Prathama S. Mainkar,

^ab Kiranmai Nayani

*^a and Srivari Chandrasekhar

*^ab

Author affiliations

* Corresponding authors

^a Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
E-mail: kiranmainayani@iict.res.in, srivaric@iict.res.in

^b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India

Abstract

An efficient Mn-catalyzed cascade azide radical addition/cyclization/oxygen insertion reaction of alkyne-tethered cyclohexadienones with TMSN₃ under mild conditions is reported. This domino reaction presents good diastereoselectivity generating bicyclic azido alcohol scaffolds which can be transformed into useful building blocks in organic synthesis for medicinal chemistry.

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Article information

DOI: https://doi.org/10.1039/D0CC00102C
Article type: Communication
Submitted: 06 Jan 2020
Accepted: 18 Feb 2020
First published: 20 Feb 2020

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Chem. Commun., 2020,56, 3453-3456

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Mn-catalyzed radical initiated domino transformation of alkynylated cyclohexadienones with TMSN₃ and O₂ to bicyclic azido alcohols

P. Pal, P. S. Mainkar, K. Nayani and S. Chandrasekhar, Chem. Commun., 2020, 56, 3453 DOI: 10.1039/D0CC00102C

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