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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance

Author(s): Julia Trossarello, Adegboyega Egunjobi, Whitney J. Morgan, Rayaj Ahamed and Karelle S. Aiken

Volume 11, Issue 3, 2014

Page: [466 - 470] Pages: 5

DOI: 10.2174/15701794113106660069

Price: $65

Abstract

Methyl ketone derivatives can be accessed from 5-oxo-1-alkynes in an iodine-initiated hydration of the terminal alkynes. Use of molecular iodine in this manner is novel, inexpensive and a greener alternative to the traditional use of transition metal catalysts. Herein, we report the results of a methodology study which sheds light on the underlying mechanism of this new, metal-free reaction. Our findings indicate that the hydration of the alkyne proceeds via an important anchimeric assistance in which the neighboring keto group participates with a 5-exo-dig cyclization.

Keywords: Anchimeric assistance, deiodination, hydration, ketone, metal-free, molecular iodine, terminal alkyne.

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