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Concise Asymmetric Synthesis of Fully Substituted Isoxazoline‐ N ‐Oxide through Lewis Base Catalyzed Nitroalkene Activation
Author(s) -
Zhong Cheng,
Gautam Lekh Nath S.,
Petersen Jeffrey L.,
Akhmedov Novruz G.,
Shi Xiaodong
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001237
Subject(s) - nitroalkene , catalysis , lewis acids and bases , base (topology) , chemistry , oxide , organic chemistry , enantioselective synthesis , mathematics , mathematical analysis
Transforming isoxazoline‐ N ‐oxides : A concise asymmetric synthesis of isoxazoline‐ N ‐oxides is reported through secondary amine Lewis base catalyzed nitroalkene activation and sequential intermolecular condensation with aldehydes and ylides. Application of camphor‐derived chiral sulfur ylides gave the enantiomeric‐enriched isoxazoline‐ N ‐oxides in excellent yields and stereoselectivity. Simple transformations of isoxazoline‐ N ‐oxide led to the gram‐scale synthesis of a (−)‐clausenamide analogue in four steps, with excellent stereochemistry control (see scheme).