Diastereoselective Synthesis of Spirocyclic Dihydrofurans and 1-Oxaspiro[4.5]decan-6-one Derivatives from Norbornyl α-Diketones

Mahadevegowda, S H and Khan, Faiz Ahmed (2015) Diastereoselective Synthesis of Spirocyclic Dihydrofurans and 1-Oxaspiro[4.5]decan-6-one Derivatives from Norbornyl α-Diketones. European Journal of Organic Chemistry (4). pp. 858-870. ISSN 1434-193X

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Abstract

A diastereoselective zinc-mediated propargylation of non-enolizable norbornyl α-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting α-keto homopropargyl alcohols with terminal alkynes leading to spirocyclic dihydrofurans have been reported. The dihydrofurans obtained were subjected to hydrogenation to afford spiro tetrahydrofuran derivatives in nearly quantitative yields (98-99%). Eventually, the prepared α-spiro tetrahydrofuran norbornyl monoketones were utilized as precursors for acid-mediated Grob-type fragmentation reactions and converted into 1-oxaspiro[4.5]decan-6-one derivatives by treatment with p-toluenesulfonic acid.

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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	Synthetic methods; Diastereo­selectivity; Oxygen heterocycles; Spiro compounds; Ketones
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	19 Jan 2015 09:18
Last Modified:	21 Sep 2017 06:23
URI:	http://raiithold.iith.ac.in/id/eprint/1322
Publisher URL:	https://doi.org/10.1002/ejoc.201403087
OA policy:	http://www.sherpa.ac.uk/romeo/issn/1434-193X/
Related URLs:	Google Scholar

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