Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates



Barday, M, Ho, KYT, Halsall, CT and Aissa, C ORCID: 0000-0003-0750-9435
(2016) Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates. Organic Letters, 18 (8). 1756 - 1759.

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Abstract

The poor regioselectivity of the [4 + 2] cycloaddition of 3-azetidinones with internal alkynes bearing two alkyl substituents via nickel-catalyzed carbon–carbon activation is addressed using 1,3-enynes as substrates. The judicious choice of substitution on the enyne enables complementary access to each regioisomer of 3-hydroxy-4,5-alkyl-substituted pyridines, which are important building blocks in medicinal chemistry endeavors.

Item Type: Article
Uncontrolled Keywords: Hydrocarbons, Pyridines, cyclization, Hydrogenation Selectivity
Depositing User: Symplectic Admin
Date Deposited: 27 Apr 2016 16:10
Last Modified: 13 Nov 2020 14:34
DOI: 10.1021/acs.orglett.6b00451
Related URLs:
URI: http://livrepository.liverpool.ac.uk/id/eprint/3000670