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). pp. 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:	19 Jan 2023 07:37
DOI:	10.1021/acs.orglett.6b00451
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3000670