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1,3‐Dipolar Cycloadditions of β‐Fluoroalkyl Vinylsulfones and Nitrile Oxides for Fluoroalkylated Isoxazolines and Isoxazoles
Author(s) -
Ou Zhi,
Huang Qian,
Kou YingDa,
Cheng Feng,
Kalita Subarna Jyoti,
Zhao ZhenNi,
Huang YiYong
Publication year - 2019
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.201900578
Subject(s) - chemistry , nitrile , yield (engineering) , organic chemistry , polymer chemistry , medicinal chemistry , combinatorial chemistry , metallurgy , materials science
Abstract The 1,3‐dipolar cycloadditions of β‐fluoroalkyl vinylsulfones and nitrile oxides to deliver 5‐fluoroalkyl‐3‐substituted 2‐isoxazolines has been established under mild conditions in up to 85% yield with excellent regio‐ and diastereoselectivities (all d.r. >99 : 1), and thus facilitated rapid access to 5‐fluoroalkyl‐3‐Ph‐2‐isoxazoles by DBU‐mediated elimination of the pyridyl sulfone group.