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Chemoselective Formal [4+2] Cycloaddition of 3‐Hydroxycyclobutanones with Enones
Author(s) -
Harada Kosuke,
Nowaki Aya,
Matsuo Junichi
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300156
Subject(s) - chemistry , cycloaddition , cyclohexanone , double bond , boron trifluoride , lewis acids and bases , organic chemistry , catalysis
Choice cuts : The formal [4+2] cycloaddition of 3‐hydroxycyclobutanones to α,β‐unsaturated ketones proceeds chemoselectively at the α,β‐carbon–carbon double bond to afford cyclohexanone derivatives by using boron trifluoride etherate as a Lewis acid. In contrast, 3‐ethoxycyclobutanone reacts at the carbonyl carbon–oxygen double bond to give dihydro‐γ‐pyrones.