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Catalytic Asymmetric Synthesis of 2‐Alkyleneoxetanes through [2+2] Annulation of Allenoates with Trifluoromethyl Ketones
Author(s) -
Zhao QianYi,
Huang Long,
Wei Yin,
Shi Min
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200237
Subject(s) - trifluoromethyl , chemistry , annulation , enantioselective synthesis , dihydropyran , catalysis , organic chemistry , combinatorial chemistry , optically active , alkyl
Abstract The first example of a β‐isocupreidine (β‐ICD)‐catalyzed highly enantioselective [2+2] annulation of allenoates with trifluoromethyl ketones has been disclosed, allowing the synthesis of optically active 2‐alkyleneoxetanes in moderate to good yields along with good to high enantioselectivities and high diastereoselectivities. Further transformations of the cycloadducts have been also disclosed to afford biologically interesting 6‐trifluoromethyl‐5,6‐dihydropyran‐2‐ones and trifluoromethyl β‐keto acids in good yields.